NPASS Compound

Structure

CID326027 OpenBabel06191716182D 110113 0 0 1 0 0 0 0 0999 V2000 -24.1512 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1759 -6.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9131 -1.6343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5636 -2.6956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.6347 2.6890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.6388 1.2905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.0363 -1.7551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5157 0.3815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9504 -5.5389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5038 5.8945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1897 2.5554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -1.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.7545 -0.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5223 4.3363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7567 3.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4337 -1.9825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -23.3438 2.5258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3685 -5.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.3520 -0.2712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 -0.4956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4337 0.9912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5753 1.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.4504 -0.6830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0092 -2.9766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8216 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -22.3479 1.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6950 -2.6516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7623 4.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.3603 -3.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5142 2.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9320 -1.7753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -22.4421 2.1140 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -21.4462 0.7155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.2289 -1.1802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -15.3231 -0.1934 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.0446 -4.5522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8722 4.9743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9388 3.2045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8584 -0.4956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4337 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9459 -3.3008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7169 0.9912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.4627 -4.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5509 2.5623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5075 -1.6783 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -19.6429 -0.1080 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -8.8256 5.1608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.4586 -3.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.3272 -1.5919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.9462 -4.1404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0033 -0.2788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1506 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8755 2.8803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7169 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7169 0.9912 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8584 1.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3193 -0.9962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2921 -0.4956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -16.2248 0.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1825 3.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.6553 -4.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5198 -1.0170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.0404 -3.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4575 0.6022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6879 1.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0138 4.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -0.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4976 -1.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -18.6471 -1.5066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.7413 -0.5198 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -7.1335 -4.2741 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -13.2371 -3.9772 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -16.3190 1.2051 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.5697 4.2617 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -19.4545 -2.0815 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.8355 5.2080 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -18.3644 -4.4668 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.6451 1.5756 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -14.2330 -2.5787 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -15.7537 -4.7154 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.6182 -1.4287 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7822 0.9202 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3297 3.7613 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5707 -1.3541 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.7512 4.1778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -19.7372 0.8787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0132 6.1342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.6512 -2.9051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 -0.4956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 1.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 2.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.0322 -0.3566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0409 3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.7495 -3.3168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6140 -0.0302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.9421 -2.7419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.3942 0.2780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6978 1.9541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4010 5.2579 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0793 -1.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5918 -2.7122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.7454 -1.9183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.3295 0.3818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7934 3.7471 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2921 -1.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 1.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4608 -1.4918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 13 72 1 0 0 0 0 14 85 1 0 0 0 0 15106 1 0 0 0 0 16107 1 0 0 0 0 17 33 1 0 0 0 0 18 44 2 0 0 0 0 19 24 2 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 41 2 0 0 0 0 21 23 2 0 0 0 0 21 41 1 0 0 0 0 22 43 2 0 0 0 0 23 43 1 0 0 0 0 24 47 1 0 0 0 0 25 26 1 0 0 0 0 25 42 1 0 0 0 0 26 86 1 0 0 0 0 27 33 1 0 0 0 0 27 34 2 0 0 0 0 28 42 1 0 0 0 0 29 48 1 0 0 0 0 29 76 1 0 0 0 0 30 49 1 0 0 0 0 30 77 1 0 0 0 0 31106 1 0 0 0 0 35 7 1 1 0 0 0 35 36 1 0 0 0 0 35 50 1 0 0 0 0 36 8 1 6 0 0 0 36 60 1 0 0 0 0 37 9 1 1 0 0 0 37 51 1 0 0 0 0 37 74 1 0 0 0 0 38 10 1 1 0 0 0 38 67 1 0 0 0 0 38 78 1 0 0 0 0 39 11 1 6 0 0 0 39 87 1 0 0 0 0 40 12 1 6 0 0 0 40 55 1 0 0 0 0 40108 1 0 0 0 0 41 59 1 0 0 0 0 42 73 1 6 0 0 0 43109 1 0 0 0 0 44 62 1 0 0 0 0 44 79 1 0 0 0 0 45 31 1 6 0 0 0 45 61 1 0 0 0 0 45 80 1 0 0 0 0 46 28 1 1 0 0 0 46 69 1 0 0 0 0 46 86 1 0 0 0 0 47 72 1 0 0 0 0 47 88 1 0 0 0 0 48 78 2 3 0 0 0 48 89 1 0 0 0 0 49 79 2 3 0 0 0 49 90 1 0 0 0 0 50 63 1 1 0 0 0 50 81 1 0 0 0 0 51 64 1 6 0 0 0 51 82 1 0 0 0 0 52 58 1 0 0 0 0 52 65 1 0 0 0 0 52 83 1 1 0 0 0 53 59 1 6 0 0 0 53 68 1 0 0 0 0 53 84 1 0 0 0 0 54 39 1 1 0 0 0 54 66 1 0 0 0 0 54 85 1 0 0 0 0 55 56 1 0 0 0 0 55 91 1 1 0 0 0 56 57 1 0 0 0 0 56 92 1 6 0 0 0 57 70 1 0 0 0 0 57 93 1 6 0 0 0 58 32 1 6 0 0 0 58110 1 0 0 0 0 59107 1 1 0 0 0 60 75 2 0 0 0 0 60 94 1 0 0 0 0 61 76 2 3 0 0 0 61 95 1 0 0 0 0 62 82 2 3 0 0 0 62 96 1 0 0 0 0 63 83 2 3 0 0 0 63 97 1 0 0 0 0 64 81 2 3 0 0 0 64 98 1 0 0 0 0 65 80 2 3 0 0 0 65 99 1 0 0 0 0 66 84 2 3 0 0 0 66100 1 0 0 0 0 67 85 1 0 0 0 0 67101 2 0 0 0 0 68 86 1 0 0 0 0 68102 2 0 0 0 0 69103 2 0 0 0 0 69110 1 0 0 0 0 70108 1 0 0 0 0 70109 1 1 0 0 0 71 72 1 0 0 0 0 71 77 2 3 0 0 0 71104 1 0 0 0 0 72105 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1577.76
Volume:	1538.683
LogP:	0.768
LogD:	0.457
LogS:	-1.225
# Rotatable Bonds:	31
TPSA:	578.16
# H-Bond Aceptor:	37
# H-Bond Donor:	19
# Rings:	4
# Heavy Atoms:	38

MedChem Properties

QED Drug-Likeness Score:	0.014
Synthetic Accessibility Score:	8.056
Fsp3:	0.653
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	0.0018240285571664572
Pgp-inhibitor:	0.346
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	46.83727264404297%
Volume Distribution (VD):	0.488
Pgp-substrate:	27.660709381103516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	1.194
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.283
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.907

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC326027

Natural Product ID:	NPC326027
*Common Name:**	Mirabamide E
IUPAC Name:	(2R,3S,4S)-4-[[(2S,3S)-3-amino-2-[[(Z)-2-[[2-[[(4Z,6E)-2,3-dihydroxy-2,6,8-trimethyldeca-4,6-dienoyl]amino]acetyl]amino]but-2-enoyl]amino]butanoyl]amino]-N'-[(3R,6S,9S,15R,18R,19R,22S,24S)-24-chloro-6-[(1R)-1-hydroxyethyl]-15-(methoxymethyl)-3-[(R)-methoxy-[4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]methyl]-7,9-dimethyl-2,5,8,11,14,17,21-heptaoxo-19-propan-2-yl-20-oxa-1,4,7,10,13,16-hexazabicyclo[20.4.0]hexacosan-18-yl]-2,3-dimethylpentanediamide
Synonyms:	Mirabamide E
Standard InCHIKey:	APTOZTHRCLKEEQ-OJHSLUOMSA-N
Standard InCHI:	InChI=1S/C72H112ClN13O24/c1-17-33(5)27-34(6)19-24-47(88)72(13,105)71(104)77-30-49(90)79-44(18-2)62(96)82-51(37(9)74)64(98)81-50(35(7)36(8)60(75)94)63(97)83-52-58(32(3)4)110-69(103)46-28-42(73)25-26-86(46)68(102)53(59(107-16)41-20-22-43(23-21-41)109-70-57(93)56(92)55(91)40(12)108-70)84-66(100)54(39(11)87)85(14)67(101)38(10)78-48(89)29-76-61(95)45(31-106-15)80-65(52)99/h18-24,27,32-33,35-40,42,45-47,50-59,70,87-88,91-93,105H,17,25-26,28-31,74H2,1-16H3,(H2,75,94)(H,76,95)(H,77,104)(H,78,89)(H,79,90)(H,80,99)(H,81,98)(H,82,96)(H,83,97)(H,84,100)/b24-19-,34-27+,44-18-/t33?,35-,36+,37-,38-,39+,40-,42-,45+,46-,47?,50-,51-,52+,53+,54-,55-,56+,57+,58+,59+,70-,72?/m0/s1
SMILES:	CCC(C)C=C(C)C=CC(C(C)(C(=O)NCC(=O)NC(=CC)C(=O)NC(C(C)N)C(=O)NC(C(C)C(C)C(=O)N)C(=O)NC1C(OC(=O)C2CC(CCN2C(=O)C(NC(=O)C(N(C(=O)C(NC(=O)CNC(=O)C(NC1=O)COC)C)C)C(C)O)C(C3=CC=C(C=C3)OC4C(C(C(C(O4)C)O)O)O)OC)Cl)C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689426
PubChem CID:	51041750
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides [CHEMONTID:0002250] Cyclic glycodepsipeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21214233]
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21214233]
NPO14376	Stephania cephalantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	121.0	nM	PMID[571187]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC326027 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	1311
0.2-0.3	4846
0.3-0.4	11420
0.4-0.5	10735
0.5-0.6	12910
0.6-0.7	1074
0.7-0.8	140
0.8-0.85	6
0.85-0.9	2
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC326333
0.9158	High Similarity	NPC323662
0.8947	High Similarity	NPC328763
0.8109	Intermediate Similarity	NPC477552
0.8109	Intermediate Similarity	NPC477550
0.803	Intermediate Similarity	NPC477551
0.7892	Intermediate Similarity	NPC123859
0.7864	Intermediate Similarity	NPC311357
0.7854	Intermediate Similarity	NPC242728
0.7812	Intermediate Similarity	NPC196091
0.7801	Intermediate Similarity	NPC209463
0.7794	Intermediate Similarity	NPC144314
0.7756	Intermediate Similarity	NPC50548
0.7755	Intermediate Similarity	NPC194671
0.7755	Intermediate Similarity	NPC269750
0.7745	Intermediate Similarity	NPC149962
0.7739	Intermediate Similarity	NPC315542
0.772	Intermediate Similarity	NPC473693
0.772	Intermediate Similarity	NPC471568
0.7688	Intermediate Similarity	NPC471050
0.7688	Intermediate Similarity	NPC471048
0.7688	Intermediate Similarity	NPC471049
0.7653	Intermediate Similarity	NPC50016
0.765	Intermediate Similarity	NPC299806
0.7641	Intermediate Similarity	NPC248670
0.7602	Intermediate Similarity	NPC279871
0.7602	Intermediate Similarity	NPC158277
0.76	Intermediate Similarity	NPC294951
0.7551	Intermediate Similarity	NPC306804
0.7551	Intermediate Similarity	NPC273755
0.7549	Intermediate Similarity	NPC473378
0.7549	Intermediate Similarity	NPC473407
0.7547	Intermediate Similarity	NPC194699
0.7547	Intermediate Similarity	NPC219350
0.7538	Intermediate Similarity	NPC46009
0.7513	Intermediate Similarity	NPC471165
0.75	Intermediate Similarity	NPC473305
0.75	Intermediate Similarity	NPC163961
0.7488	Intermediate Similarity	NPC473371
0.7487	Intermediate Similarity	NPC475421
0.7487	Intermediate Similarity	NPC45037
0.7487	Intermediate Similarity	NPC186617
0.7419	Intermediate Similarity	NPC25539
0.7407	Intermediate Similarity	NPC277306
0.7407	Intermediate Similarity	NPC469442
0.7379	Intermediate Similarity	NPC248822
0.7379	Intermediate Similarity	NPC477526
0.7376	Intermediate Similarity	NPC167763
0.7376	Intermediate Similarity	NPC470112
0.7376	Intermediate Similarity	NPC470903
0.736	Intermediate Similarity	NPC475123
0.736	Intermediate Similarity	NPC475204
0.7337	Intermediate Similarity	NPC26108
0.7337	Intermediate Similarity	NPC473354
0.733	Intermediate Similarity	NPC61332
0.733	Intermediate Similarity	NPC240130
0.7308	Intermediate Similarity	NPC302715
0.7286	Intermediate Similarity	NPC137627
0.7282	Intermediate Similarity	NPC102959
0.7273	Intermediate Similarity	NPC40234
0.7268	Intermediate Similarity	NPC276120
0.7264	Intermediate Similarity	NPC469443
0.7259	Intermediate Similarity	NPC107938
0.7259	Intermediate Similarity	NPC294516
0.725	Intermediate Similarity	NPC473402
0.725	Intermediate Similarity	NPC159767
0.725	Intermediate Similarity	NPC476227
0.725	Intermediate Similarity	NPC155506
0.7246	Intermediate Similarity	NPC60516
0.7245	Intermediate Similarity	NPC472923
0.7245	Intermediate Similarity	NPC63931
0.7241	Intermediate Similarity	NPC476321
0.7241	Intermediate Similarity	NPC473404
0.7236	Intermediate Similarity	NPC230611
0.7208	Intermediate Similarity	NPC254700
0.7206	Intermediate Similarity	NPC471526
0.7183	Intermediate Similarity	NPC473450
0.7172	Intermediate Similarity	NPC473502
0.7165	Intermediate Similarity	NPC187028
0.7165	Intermediate Similarity	NPC56635
0.7165	Intermediate Similarity	NPC197741
0.7165	Intermediate Similarity	NPC305700
0.7165	Intermediate Similarity	NPC140915
0.7165	Intermediate Similarity	NPC10221
0.7165	Intermediate Similarity	NPC18249
0.7164	Intermediate Similarity	NPC477462
0.715	Intermediate Similarity	NPC476741
0.7143	Intermediate Similarity	NPC65714
0.7143	Intermediate Similarity	NPC220060
0.7136	Intermediate Similarity	NPC138083
0.7098	Intermediate Similarity	NPC476742
0.7083	Intermediate Similarity	NPC476744
0.7081	Intermediate Similarity	NPC29531
0.7081	Intermediate Similarity	NPC64140
0.7081	Intermediate Similarity	NPC174122
0.7065	Intermediate Similarity	NPC89831
0.7065	Intermediate Similarity	NPC328494
0.7062	Intermediate Similarity	NPC314083
0.7042	Intermediate Similarity	NPC471592
0.7041	Intermediate Similarity	NPC319320
0.7041	Intermediate Similarity	NPC287757
0.7033	Intermediate Similarity	NPC234069
0.7032	Intermediate Similarity	NPC469444
0.7031	Intermediate Similarity	NPC476743
0.7028	Intermediate Similarity	NPC184933
0.7028	Intermediate Similarity	NPC471563
0.7028	Intermediate Similarity	NPC59827
0.7024	Intermediate Similarity	NPC32064
0.7014	Intermediate Similarity	NPC92235
0.7014	Intermediate Similarity	NPC469445
0.7012	Intermediate Similarity	NPC319774
0.7	Intermediate Similarity	NPC153365
0.7	Intermediate Similarity	NPC314743
0.6995	Remote Similarity	NPC164608
0.6986	Remote Similarity	NPC94862
0.6986	Remote Similarity	NPC257266
0.6959	Remote Similarity	NPC139699
0.6959	Remote Similarity	NPC114659
0.6955	Remote Similarity	NPC257728
0.6955	Remote Similarity	NPC478005
0.6943	Remote Similarity	NPC324081
0.6935	Remote Similarity	NPC471051
0.6935	Remote Similarity	NPC471052
0.6935	Remote Similarity	NPC471053
0.693	Remote Similarity	NPC477527
0.6923	Remote Similarity	NPC470902
0.6919	Remote Similarity	NPC476194
0.6919	Remote Similarity	NPC283207
0.6916	Remote Similarity	NPC274268
0.6911	Remote Similarity	NPC178466
0.6911	Remote Similarity	NPC63628
0.6908	Remote Similarity	NPC477637
0.69	Remote Similarity	NPC252156
0.6875	Remote Similarity	NPC314656
0.6872	Remote Similarity	NPC473341
0.6866	Remote Similarity	NPC61004
0.6866	Remote Similarity	NPC471337
0.6849	Remote Similarity	NPC473460
0.6847	Remote Similarity	NPC293347
0.6842	Remote Similarity	NPC469360
0.6842	Remote Similarity	NPC315913
0.6842	Remote Similarity	NPC478007
0.6839	Remote Similarity	NPC9373
0.6835	Remote Similarity	NPC214368
0.6834	Remote Similarity	NPC469243
0.6832	Remote Similarity	NPC328649
0.6827	Remote Similarity	NPC314025
0.6825	Remote Similarity	NPC4910
0.6818	Remote Similarity	NPC473422
0.6816	Remote Similarity	NPC223207
0.6814	Remote Similarity	NPC471335
0.681	Remote Similarity	NPC248903
0.6806	Remote Similarity	NPC195814
0.6804	Remote Similarity	NPC245974
0.6802	Remote Similarity	NPC244509
0.6802	Remote Similarity	NPC473580
0.6794	Remote Similarity	NPC314213
0.6789	Remote Similarity	NPC476661
0.6788	Remote Similarity	NPC135121
0.6784	Remote Similarity	NPC244336
0.6783	Remote Similarity	NPC478008
0.6782	Remote Similarity	NPC304074
0.6782	Remote Similarity	NPC290755
0.6782	Remote Similarity	NPC471771
0.6771	Remote Similarity	NPC201244
0.6771	Remote Similarity	NPC477217
0.677	Remote Similarity	NPC66191
0.677	Remote Similarity	NPC314817
0.677	Remote Similarity	NPC316297
0.6769	Remote Similarity	NPC475168
0.6769	Remote Similarity	NPC7817
0.6767	Remote Similarity	NPC26928
0.6758	Remote Similarity	NPC476662
0.6757	Remote Similarity	NPC79130
0.6754	Remote Similarity	NPC91953
0.675	Remote Similarity	NPC475544
0.675	Remote Similarity	NPC471527
0.6745	Remote Similarity	NPC329731
0.6743	Remote Similarity	NPC267414
0.6736	Remote Similarity	NPC81026
0.6734	Remote Similarity	NPC207675
0.6734	Remote Similarity	NPC197743
0.6734	Remote Similarity	NPC212699
0.6734	Remote Similarity	NPC297145
0.6724	Remote Similarity	NPC475624
0.6723	Remote Similarity	NPC213529
0.6723	Remote Similarity	NPC3921
0.6718	Remote Similarity	NPC132771
0.6713	Remote Similarity	NPC475843
0.671	Remote Similarity	NPC148124
0.6702	Remote Similarity	NPC469426
0.6702	Remote Similarity	NPC469427
0.6702	Remote Similarity	NPC197921
0.6701	Remote Similarity	NPC247298
0.67	Remote Similarity	NPC469479
0.6698	Remote Similarity	NPC291759
0.6684	Remote Similarity	NPC266741
0.6683	Remote Similarity	NPC198254
0.6683	Remote Similarity	NPC274198
0.6681	Remote Similarity	NPC475565

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC326027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	489
0.2-0.3	922
0.3-0.4	2209
0.4-0.5	2865
0.5-0.6	2177
0.6-0.7	337
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7538	Intermediate Similarity	NPD7608	Discontinued
0.7245	Intermediate Similarity	NPD8031	Discontinued
0.7217	Intermediate Similarity	NPD7810	Phase 3
0.7217	Intermediate Similarity	NPD7811	Phase 3
0.7135	Intermediate Similarity	NPD7131	Phase 3
0.705	Intermediate Similarity	NPD7485	Phase 3
0.705	Intermediate Similarity	NPD7484	Phase 3
0.7005	Intermediate Similarity	NPD7972	Discontinued
0.6986	Remote Similarity	NPD7583	Approved
0.6971	Remote Similarity	NPD6853	Approved
0.6971	Remote Similarity	NPD6851	Approved
0.6955	Remote Similarity	NPD7585	Approved
0.6943	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7565	Approved
0.6883	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8059	Phase 3
0.6842	Remote Similarity	NPD7978	Discontinued
0.6833	Remote Similarity	NPD7584	Approved
0.6827	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6312	Discontinued
0.6789	Remote Similarity	NPD2239	Approved
0.6789	Remote Similarity	NPD2240	Approved
0.6779	Remote Similarity	NPD6297	Approved
0.677	Remote Similarity	NPD7930	Approved
0.6745	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6863	Phase 2
0.6712	Remote Similarity	NPD7999	Approved
0.6711	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7783	Phase 2
0.6684	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3536	Discontinued
0.6683	Remote Similarity	NPD8417	Discontinued
0.6681	Remote Similarity	NPD7827	Phase 1
0.6667	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5772	Approved
0.6667	Remote Similarity	NPD5773	Approved
0.6652	Remote Similarity	NPD8162	Phase 2
0.6652	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6072	Discontinued
0.665	Remote Similarity	NPD6677	Suspended
0.665	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7801	Approved
0.6635	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6681	Discovery
0.6619	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5355	Approved
0.6617	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD5356	Approved
0.6599	Remote Similarity	NPD6419	Discontinued
0.6591	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2904	Discontinued
0.6584	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD5756	Phase 2
0.6577	Remote Similarity	NPD6823	Phase 2
0.6575	Remote Similarity	NPD6034	Phase 2
0.6573	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6905	Phase 2
0.6561	Remote Similarity	NPD5745	Approved
0.6558	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8491	Approved
0.6553	Remote Similarity	NPD3263	Phase 3
0.6552	Remote Similarity	NPD7318	Phase 3
0.6542	Remote Similarity	NPD3153	Approved
0.6542	Remote Similarity	NPD3154	Approved
0.653	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7280	Phase 3
0.6526	Remote Similarity	NPD7281	Phase 3
0.6525	Remote Similarity	NPD8469	Approved
0.6524	Remote Similarity	NPD8366	Approved
0.6518	Remote Similarity	NPD7891	Discontinued
0.6504	Remote Similarity	NPD7701	Phase 2
0.6497	Remote Similarity	NPD5295	Discontinued
0.6497	Remote Similarity	NPD3122	Phase 3
0.6493	Remote Similarity	NPD5485	Approved
0.6493	Remote Similarity	NPD5484	Approved
0.6484	Remote Similarity	NPD7256	Discontinued
0.6474	Remote Similarity	NPD1423	Approved
0.6473	Remote Similarity	NPD6107	Approved
0.6462	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD8303	Discontinued
0.6455	Remote Similarity	NPD5746	Approved
0.6453	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7317	Phase 3
0.6453	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2122	Discontinued
0.6445	Remote Similarity	NPD5312	Approved
0.6445	Remote Similarity	NPD5313	Approved
0.6435	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7038	Approved
0.6432	Remote Similarity	NPD7039	Approved
0.6432	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3687	Approved
0.6418	Remote Similarity	NPD3686	Approved
0.6418	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5557	Phase 1
0.6413	Remote Similarity	NPD6519	Phase 2
0.6411	Remote Similarity	NPD5137	Approved
0.6404	Remote Similarity	NPD8151	Discontinued
0.6402	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.64	Remote Similarity	NPD52	Approved
0.64	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7526	Approved
0.6393	Remote Similarity	NPD7296	Approved
0.6389	Remote Similarity	NPD8255	Phase 2
0.6385	Remote Similarity	NPD7007	Discovery
0.6384	Remote Similarity	NPD7476	Discontinued
0.638	Remote Similarity	NPD5582	Discontinued
0.6377	Remote Similarity	NPD6315	Phase 2
0.6373	Remote Similarity	NPD3054	Approved
0.6373	Remote Similarity	NPD8019	Approved
0.6373	Remote Similarity	NPD3052	Approved
0.6372	Remote Similarity	NPD8320	Phase 1
0.6372	Remote Similarity	NPD8319	Approved
0.6368	Remote Similarity	NPD3933	Discontinued
0.6368	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6042	Phase 2
0.6368	Remote Similarity	NPD5096	Phase 3
0.6368	Remote Similarity	NPD5095	Phase 3
0.6368	Remote Similarity	NPD3136	Phase 2
0.6368	Remote Similarity	NPD42	Phase 2
0.6368	Remote Similarity	NPD6874	Approved
0.6368	Remote Similarity	NPD3179	Approved
0.6368	Remote Similarity	NPD3180	Approved
0.6364	Remote Similarity	NPD8323	Discontinued
0.6356	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD3366	Approved
0.635	Remote Similarity	NPD3985	Discontinued
0.6347	Remote Similarity	NPD6505	Approved
0.6347	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6504	Approved
0.6346	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4666	Phase 3
0.6346	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5640	Discontinued
0.6344	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6045	Phase 3
0.6341	Remote Similarity	NPD8455	Phase 2
0.6335	Remote Similarity	NPD4360	Phase 2
0.6335	Remote Similarity	NPD4363	Phase 3
0.6333	Remote Similarity	NPD2388	Discontinued
0.633	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3490	Discontinued
0.6329	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7697	Approved
0.6327	Remote Similarity	NPD3656	Approved
0.6327	Remote Similarity	NPD7698	Approved
0.6327	Remote Similarity	NPD7696	Phase 3
0.6324	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6620	Discovery
0.6321	Remote Similarity	NPD3909	Discontinued
0.632	Remote Similarity	NPD8152	Approved
0.632	Remote Similarity	NPD8153	Approved
0.6318	Remote Similarity	NPD6390	Discontinued
0.6318	Remote Similarity	NPD7613	Discontinued
0.6313	Remote Similarity	NPD2575	Approved
0.631	Remote Similarity	NPD8370	Discontinued
0.6308	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5709	Phase 3
0.6291	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4466	Phase 1
0.629	Remote Similarity	NPD5150	Phase 2
0.6287	Remote Similarity	NPD7523	Phase 3
0.6286	Remote Similarity	NPD7315	Approved
0.6276	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD1725	Approved
0.6272	Remote Similarity	NPD8161	Suspended
0.6271	Remote Similarity	NPD8479	Phase 2
0.6267	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2977	Approved
0.6262	Remote Similarity	NPD2978	Approved
0.6256	Remote Similarity	NPD4157	Discontinued
0.6256	Remote Similarity	NPD2215	Approved
0.6256	Remote Similarity	NPD2216	Approved
0.6256	Remote Similarity	NPD6852	Discontinued
0.6256	Remote Similarity	NPD6669	Phase 2
0.625	Remote Similarity	NPD4420	Approved
0.625	Remote Similarity	NPD6667	Approved
0.625	Remote Similarity	NPD6666	Approved
0.625	Remote Similarity	NPD8070	Approved
0.625	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7043	Discontinued
0.6244	Remote Similarity	NPD3819	Phase 2
0.6235	Remote Similarity	NPD8461	Discontinued
0.6234	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7874	Approved
0.6233	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD4361	Phase 2
0.6232	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5481	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data