NPASS Compound

Structure

CID319774 OpenBabel06191716152D 111121 0 0 1 0 0 0 0 0999 V2000 -7.1412 2.6657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8938 4.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8685 -10.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6803 1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3635 -7.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2857 -2.0254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8488 0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6051 -4.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9869 1.6644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1904 -5.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0227 -4.6447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0792 1.2884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3644 -4.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8392 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7569 -3.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6246 0.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9030 -5.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3845 -2.2041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2779 -3.2046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1808 -3.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7872 -2.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3886 -2.7499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9853 -7.6349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0513 -1.3877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5168 1.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9581 3.2115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2408 -9.4533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4706 0.5319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1216 -4.5077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9693 1.6644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2101 -5.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0792 -2.8988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1723 -2.8510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1337 -3.5428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8040 -3.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4743 -0.0086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6537 -4.0790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9035 1.7966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5717 -2.2041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8128 -4.0670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4104 -2.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3845 0.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2886 -3.8228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0085 -1.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5392 -2.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2097 0.9598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2697 -2.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0117 -7.7671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3249 -0.7263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4189 -3.5512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1301 -5.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9869 -3.2748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4539 -4.5392 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5717 0.5937 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4503 -6.2189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8770 1.2884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1457 1.2582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8721 0.5967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7827 -6.0810 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4193 -1.9196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6625 -0.3631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2143 -9.3211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1970 -0.1296 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0866 1.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8770 -2.8988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7090 -5.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2791 -3.8907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9476 -0.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8271 -5.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4499 -4.0531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7264 -0.6615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5865 -8.4119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9874 -1.0894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4192 -0.9895 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.3509 -3.3868 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -8.0866 -2.8612 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4957 -8.7841 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9472 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.7846 1.3621 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9476 -1.2964 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9693 -3.2748 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3291 -4.5705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4623 -5.2540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2054 1.6853 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1227 -6.1064 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3071 2.5811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6842 -2.3699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8353 -3.9685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2554 -2.3352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3339 -1.3350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4228 2.1053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3554 2.2180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8082 0.8950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8155 -10.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1331 0.1688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1508 0.2705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4228 -3.7157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3569 -6.4971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2290 -3.6398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9112 -0.1223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1406 -6.5717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1364 -4.7559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7154 -3.1072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6395 -8.6763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5346 0.2336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0085 -0.3140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0268 -3.2185 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 -0.4105 -6.9902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3889 -1.0246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5168 -1.6213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 7 79 1 0 0 0 0 8 11 2 0 0 0 0 8 29 1 0 0 0 0 9 12 2 0 0 0 0 9 30 1 0 0 0 0 10 13 2 0 0 0 0 10 31 1 0 0 0 0 11 40 1 0 0 0 0 12 42 1 0 0 0 0 13 43 1 0 0 0 0 14 26 1 0 0 0 0 15 29 2 0 0 0 0 15 34 1 0 0 0 0 16 30 2 0 0 0 0 16 36 1 0 0 0 0 17 31 2 0 0 0 0 17 37 1 0 0 0 0 18 32 2 0 0 0 0 18 44 1 0 0 0 0 19 32 1 0 0 0 0 19 45 2 0 0 0 0 20 33 2 0 0 0 0 20 35 1 0 0 0 0 21 33 1 0 0 0 0 21 41 2 0 0 0 0 22 47 1 0 0 0 0 23 48 1 0 0 0 0 23 72 1 0 0 0 0 24 49 1 0 0 0 0 24 73 1 0 0 0 0 25 86 1 0 0 0 0 27 3 1 1 0 0 0 27 62 1 0 0 0 0 27104 1 0 0 0 0 28 4 1 1 0 0 0 28 63 1 0 0 0 0 28105 1 0 0 0 0 30 56 1 0 0 0 0 31 59 1 0 0 0 0 33 87 1 0 0 0 0 34 40 2 0 0 0 0 34 50 1 0 0 0 0 35 50 2 0 0 0 0 35 53 1 0 0 0 0 36 42 2 0 0 0 0 36 74 1 0 0 0 0 37 43 2 0 0 0 0 37 75 1 0 0 0 0 38 14 1 6 0 0 0 38 64 1 0 0 0 0 38 79 1 0 0 0 0 39 22 1 6 0 0 0 39 65 1 0 0 0 0 39 80 1 0 0 0 0 40 88 1 0 0 0 0 41 50 1 0 0 0 0 41 89 1 0 0 0 0 42106 1 0 0 0 0 43107 1 0 0 0 0 44 60 2 0 0 0 0 44106 1 0 0 0 0 45 60 1 0 0 0 0 45107 1 0 0 0 0 46 25 1 6 0 0 0 46 57 1 0 0 0 0 46108 1 0 0 0 0 47 76 2 0 0 0 0 47 90 1 0 0 0 0 48104 1 0 0 0 0 48109 1 6 0 0 0 49105 1 0 0 0 0 49110 1 6 0 0 0 51 29 1 1 0 0 0 51 66 1 0 0 0 0 51 82 1 0 0 0 0 52 32 1 6 0 0 0 52 67 1 0 0 0 0 52 81 1 0 0 0 0 53 70 1 1 0 0 0 53 83 1 0 0 0 0 54 56 1 0 0 0 0 54 68 1 0 0 0 0 54 84 1 6 0 0 0 55 59 1 0 0 0 0 55 69 1 1 0 0 0 55 85 1 0 0 0 0 56 91 1 6 0 0 0 57 58 1 0 0 0 0 57 92 1 1 0 0 0 58 61 1 0 0 0 0 58 93 1 6 0 0 0 59109 1 1 0 0 0 60111 1 0 0 0 0 61 71 1 0 0 0 0 61110 1 1 0 0 0 62 72 1 6 0 0 0 62 94 1 0 0 0 0 63 73 1 6 0 0 0 63 95 1 0 0 0 0 64 84 2 3 0 0 0 64 96 1 0 0 0 0 65 81 2 3 0 0 0 65 97 1 0 0 0 0 66 85 2 3 0 0 0 66 98 1 0 0 0 0 67 82 2 3 0 0 0 67 99 1 0 0 0 0 68 80 2 3 0 0 0 68100 1 0 0 0 0 69 83 2 3 0 0 0 69101 1 0 0 0 0 70102 2 0 0 0 0 70103 1 0 0 0 0 71108 1 0 0 0 0 71111 1 6 0 0 0 72 5 1 6 0 0 0 72 77 1 0 0 0 0 73 6 1 6 0 0 0 73 78 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1590.52
Volume:	1485.339
LogP:	1.565
LogD:	0.684
LogS:	-5.947
# Rotatable Bonds:	15
TPSA:	603.43
# H-Bond Aceptor:	36
# H-Bond Donor:	26
# Rings:	13
# Heavy Atoms:	38

MedChem Properties

QED Drug-Likeness Score:	0.044
Synthetic Accessibility Score:	8.795
Fsp3:	0.438
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:	-6.312
MDCK Permeability:	3.822142389253713e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.957
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	78.2584457397461%
Volume Distribution (VD):	0.729
Pgp-substrate:	13.311738967895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	-0.422
Half-life (T1/2):	0.565

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.998
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.448
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC319774

Natural Product ID:	NPC319774
*Common Name:**	Chloroeremomycin
IUPAC Name:	n.a.
Synonyms:	Chloroeremomycin
Standard InCHIKey:	XJHXLMVKYIVZTE-LOALFDMRSA-N
Standard InCHI:	InChI=1S/C73H88Cl2N10O26/c1-26(2)14-38(79-7)64(96)84-54-56(91)30-9-12-42(36(74)16-30)106-44-18-32-19-45(60(44)111-71-61(58(93)57(92)46(25-86)108-71)110-49-24-73(6,78)63(95)28(4)105-49)107-43-13-10-31(17-37(43)75)59(109-48-23-72(5,77)62(94)27(3)104-48)55-69(101)83-53(70(102)103)35-20-33(87)21-41(89)50(35)34-15-29(8-11-40(34)88)51(66(98)85-55)82-67(99)52(32)81-65(97)39(22-47(76)90)80-68(54)100/h8-13,15-21,26-28,38-39,46,48-49,51-59,61-63,71,79,86-89,91-95H,14,22-25,77-78H2,1-7H3,(H2,76,90)(H,80,100)(H,81,97)(H,82,99)(H,83,101)(H,84,96)(H,85,98)(H,102,103)/t27-,28-,38+,39-,46+,48-,49-,51+,52+,53-,54+,55-,56+,57+,58-,59+,61+,62-,63-,71-,72-,73-/m0/s1
SMILES:	CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C7C(=O)NC(C8=C(C(=CC(=C8)O)O)C9=C(C=CC(=C9)C(C(=O)N7)NC(=O)C5NC(=O)C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC(=O)C(CC(C)C)NC)CC(=O)N)O)C(=O)O)OC1CC(C(C(O1)C)O)(C)N)Cl)CO)O)O)(C)N)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1688951
PubChem CID:	445806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO13547	Actinoplanes sp. ATCC 53771	Strain	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8326323]
NPO13547	Actinoplanes sp. ATCC 53771	Strain	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[Article]
NPO13547	Actinoplanes sp. ATCC 53771	Strain	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[501261]

☑ 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 NPC319774 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	412
0.1-0.2	1918
0.2-0.3	7270
0.3-0.4	10711
0.4-0.5	8970
0.5-0.6	11260
0.6-0.7	2134
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.991	High Similarity	NPC314743
0.7917	Intermediate Similarity	NPC3921
0.7917	Intermediate Similarity	NPC213529
0.783	Intermediate Similarity	NPC252156
0.7597	Intermediate Similarity	NPC329480
0.7577	Intermediate Similarity	NPC323858
0.746	Intermediate Similarity	NPC131258
0.7385	Intermediate Similarity	NPC313627
0.7344	Intermediate Similarity	NPC133864
0.7313	Intermediate Similarity	NPC256124
0.7236	Intermediate Similarity	NPC316461
0.7231	Intermediate Similarity	NPC473786
0.7229	Intermediate Similarity	NPC242728
0.7178	Intermediate Similarity	NPC82056
0.7167	Intermediate Similarity	NPC38964
0.7155	Intermediate Similarity	NPC315253
0.7149	Intermediate Similarity	NPC191132
0.7149	Intermediate Similarity	NPC60295
0.7143	Intermediate Similarity	NPC50548
0.7105	Intermediate Similarity	NPC175890
0.7105	Intermediate Similarity	NPC274661
0.7105	Intermediate Similarity	NPC11296
0.7105	Intermediate Similarity	NPC82457
0.7105	Intermediate Similarity	NPC48490
0.71	Intermediate Similarity	NPC144314
0.7093	Intermediate Similarity	NPC65312
0.7093	Intermediate Similarity	NPC139783
0.7082	Intermediate Similarity	NPC469689
0.7082	Intermediate Similarity	NPC471031
0.7074	Intermediate Similarity	NPC475754
0.7071	Intermediate Similarity	NPC326333
0.7061	Intermediate Similarity	NPC22115
0.7061	Intermediate Similarity	NPC275680
0.7059	Intermediate Similarity	NPC46990
0.7059	Intermediate Similarity	NPC153365
0.7056	Intermediate Similarity	NPC149962
0.7048	Intermediate Similarity	NPC95426
0.7048	Intermediate Similarity	NPC302245
0.7048	Intermediate Similarity	NPC16357
0.7043	Intermediate Similarity	NPC24260
0.7039	Intermediate Similarity	NPC123859
0.7033	Intermediate Similarity	NPC85735
0.7031	Intermediate Similarity	NPC281581
0.7017	Intermediate Similarity	NPC257728
0.7012	Intermediate Similarity	NPC326027
0.7009	Intermediate Similarity	NPC475654
0.7004	Intermediate Similarity	NPC475768
0.6985	Remote Similarity	NPC172355
0.6983	Remote Similarity	NPC264302
0.6975	Remote Similarity	NPC257266
0.697	Remote Similarity	NPC269046
0.697	Remote Similarity	NPC476565
0.6957	Remote Similarity	NPC206900
0.6953	Remote Similarity	NPC234318
0.6953	Remote Similarity	NPC281629
0.6943	Remote Similarity	NPC129533
0.6943	Remote Similarity	NPC123259
0.694	Remote Similarity	NPC30182
0.694	Remote Similarity	NPC478091
0.694	Remote Similarity	NPC478092
0.694	Remote Similarity	NPC473589
0.694	Remote Similarity	NPC85381
0.6932	Remote Similarity	NPC167027
0.693	Remote Similarity	NPC167116
0.693	Remote Similarity	NPC274716
0.693	Remote Similarity	NPC254441
0.6926	Remote Similarity	NPC318805
0.6926	Remote Similarity	NPC237202
0.6926	Remote Similarity	NPC223236
0.6926	Remote Similarity	NPC259350
0.6926	Remote Similarity	NPC41122
0.692	Remote Similarity	NPC315914
0.6916	Remote Similarity	NPC239584
0.6906	Remote Similarity	NPC9309
0.6897	Remote Similarity	NPC478093
0.6897	Remote Similarity	NPC117717
0.6886	Remote Similarity	NPC258657
0.6886	Remote Similarity	NPC15414
0.6886	Remote Similarity	NPC7715
0.6886	Remote Similarity	NPC49075
0.6886	Remote Similarity	NPC290005
0.6886	Remote Similarity	NPC239824
0.6886	Remote Similarity	NPC90998
0.6886	Remote Similarity	NPC182052
0.6886	Remote Similarity	NPC251735
0.6886	Remote Similarity	NPC311973
0.6886	Remote Similarity	NPC30779
0.6886	Remote Similarity	NPC185639
0.6886	Remote Similarity	NPC223690
0.6886	Remote Similarity	NPC181796
0.6886	Remote Similarity	NPC104196
0.6886	Remote Similarity	NPC229373
0.6886	Remote Similarity	NPC42663
0.6886	Remote Similarity	NPC285931
0.6886	Remote Similarity	NPC328155
0.6886	Remote Similarity	NPC271013
0.6886	Remote Similarity	NPC290582
0.6886	Remote Similarity	NPC217748
0.6886	Remote Similarity	NPC8836
0.6886	Remote Similarity	NPC222661
0.6886	Remote Similarity	NPC279228
0.6886	Remote Similarity	NPC54654
0.6883	Remote Similarity	NPC470642
0.6883	Remote Similarity	NPC473686
0.6883	Remote Similarity	NPC475220
0.6883	Remote Similarity	NPC229817
0.6883	Remote Similarity	NPC221140
0.6883	Remote Similarity	NPC475352
0.6872	Remote Similarity	NPC475479
0.6872	Remote Similarity	NPC243454
0.687	Remote Similarity	NPC116465
0.687	Remote Similarity	NPC212237
0.6867	Remote Similarity	NPC160543
0.6867	Remote Similarity	NPC472720
0.6867	Remote Similarity	NPC472724
0.6867	Remote Similarity	NPC31208
0.6867	Remote Similarity	NPC471563
0.6867	Remote Similarity	NPC472721
0.6867	Remote Similarity	NPC469652
0.6867	Remote Similarity	NPC187632
0.6867	Remote Similarity	NPC93065
0.6865	Remote Similarity	NPC83933
0.6862	Remote Similarity	NPC314946
0.6856	Remote Similarity	NPC80956
0.6855	Remote Similarity	NPC116701
0.6853	Remote Similarity	NPC65489
0.6851	Remote Similarity	NPC477082
0.6851	Remote Similarity	NPC476358
0.685	Remote Similarity	NPC328287
0.6842	Remote Similarity	NPC67629
0.6842	Remote Similarity	NPC257269
0.6842	Remote Similarity	NPC79736
0.6842	Remote Similarity	NPC472723
0.6842	Remote Similarity	NPC286119
0.684	Remote Similarity	NPC318119
0.6829	Remote Similarity	NPC133678
0.6826	Remote Similarity	NPC8940
0.6824	Remote Similarity	NPC223534
0.6824	Remote Similarity	NPC7839
0.6824	Remote Similarity	NPC119094
0.6824	Remote Similarity	NPC290289
0.6824	Remote Similarity	NPC240200
0.6824	Remote Similarity	NPC473618
0.6824	Remote Similarity	NPC142291
0.6824	Remote Similarity	NPC158214
0.6824	Remote Similarity	NPC173872
0.682	Remote Similarity	NPC314941
0.6812	Remote Similarity	NPC299990
0.6812	Remote Similarity	NPC267549
0.6812	Remote Similarity	NPC73492
0.6805	Remote Similarity	NPC315889
0.6798	Remote Similarity	NPC119068
0.6798	Remote Similarity	NPC40496
0.6797	Remote Similarity	NPC475662
0.6797	Remote Similarity	NPC293227
0.6797	Remote Similarity	NPC473631
0.6797	Remote Similarity	NPC321916
0.6797	Remote Similarity	NPC57036
0.6797	Remote Similarity	NPC474661
0.6797	Remote Similarity	NPC475919
0.6797	Remote Similarity	NPC473717
0.6781	Remote Similarity	NPC473716
0.6781	Remote Similarity	NPC469649
0.6781	Remote Similarity	NPC475597
0.6781	Remote Similarity	NPC260521
0.6781	Remote Similarity	NPC179947
0.678	Remote Similarity	NPC83019
0.6769	Remote Similarity	NPC297574
0.6769	Remote Similarity	NPC230276
0.6767	Remote Similarity	NPC231254
0.6767	Remote Similarity	NPC29531
0.6767	Remote Similarity	NPC186546
0.6767	Remote Similarity	NPC476576
0.6766	Remote Similarity	NPC40078
0.6766	Remote Similarity	NPC97924
0.6766	Remote Similarity	NPC471091
0.6763	Remote Similarity	NPC11708
0.6763	Remote Similarity	NPC219350
0.6763	Remote Similarity	NPC194699
0.6754	Remote Similarity	NPC98583
0.6753	Remote Similarity	NPC249996
0.6753	Remote Similarity	NPC53680
0.6753	Remote Similarity	NPC125352
0.6753	Remote Similarity	NPC208797
0.6752	Remote Similarity	NPC477081
0.6752	Remote Similarity	NPC477083
0.6751	Remote Similarity	NPC267414
0.6738	Remote Similarity	NPC111490
0.6738	Remote Similarity	NPC469650
0.6738	Remote Similarity	NPC261623
0.6737	Remote Similarity	NPC204580
0.6736	Remote Similarity	NPC174140
0.6733	Remote Similarity	NPC475624
0.6726	Remote Similarity	NPC109061
0.6724	Remote Similarity	NPC132111
0.6723	Remote Similarity	NPC3474
0.6723	Remote Similarity	NPC201814
0.6723	Remote Similarity	NPC313274
0.6722	Remote Similarity	NPC80472
0.6713	Remote Similarity	NPC9482

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 NPC319774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	698
0.2-0.3	1408
0.3-0.4	2685
0.4-0.5	2756
0.5-0.6	1174
0.6-0.7	207
0.7-0.8	7
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
0.7479	Intermediate Similarity	NPD7827	Phase 1
0.746	Intermediate Similarity	NPD8152	Approved
0.746	Intermediate Similarity	NPD8153	Approved
0.7412	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7783	Phase 2
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.7231	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7801	Approved
0.7056	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7585	Approved
0.6983	Remote Similarity	NPD7930	Approved
0.6975	Remote Similarity	NPD7583	Approved
0.694	Remote Similarity	NPD6312	Discontinued
0.6886	Remote Similarity	NPD8054	Approved
0.6886	Remote Similarity	NPD8053	Approved
0.688	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8059	Phase 3
0.682	Remote Similarity	NPD8319	Approved
0.682	Remote Similarity	NPD7870	Phase 2
0.682	Remote Similarity	NPD7871	Phase 2
0.682	Remote Similarity	NPD8320	Phase 1
0.6807	Remote Similarity	NPD6823	Phase 2
0.6798	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7999	Approved
0.6778	Remote Similarity	NPD7696	Phase 3
0.6778	Remote Similarity	NPD7697	Approved
0.6778	Remote Similarity	NPD7698	Approved
0.6763	Remote Similarity	NPD7584	Approved
0.6753	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7701	Phase 2
0.6711	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8156	Discontinued
0.6681	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.668	Remote Similarity	NPD7874	Approved
0.6667	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5005	Approved
0.6667	Remote Similarity	NPD5006	Approved
0.6653	Remote Similarity	NPD6779	Approved
0.6653	Remote Similarity	NPD6778	Approved
0.6653	Remote Similarity	NPD4363	Phase 3
0.6653	Remote Similarity	NPD6777	Approved
0.6653	Remote Similarity	NPD6781	Approved
0.6653	Remote Similarity	NPD6776	Approved
0.6653	Remote Similarity	NPD6782	Approved
0.6653	Remote Similarity	NPD4360	Phase 2
0.6653	Remote Similarity	NPD6780	Approved
0.6652	Remote Similarity	NPD8252	Approved
0.6652	Remote Similarity	NPD8251	Approved
0.6652	Remote Similarity	NPD8099	Discontinued
0.6638	Remote Similarity	NPD3819	Phase 2
0.6623	Remote Similarity	NPD5096	Phase 3
0.6623	Remote Similarity	NPD5095	Phase 3
0.6623	Remote Similarity	NPD3933	Discontinued
0.6615	Remote Similarity	NPD6723	Discontinued
0.6606	Remote Similarity	NPD8455	Phase 2
0.6579	Remote Similarity	NPD7228	Approved
0.6569	Remote Similarity	NPD7700	Phase 2
0.6569	Remote Similarity	NPD7699	Phase 2
0.6555	Remote Similarity	NPD4361	Phase 2
0.6555	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD8398	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7038	Approved
0.6537	Remote Similarity	NPD7039	Approved
0.6534	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6851	Approved
0.6524	Remote Similarity	NPD6853	Approved
0.6522	Remote Similarity	NPD7074	Phase 3
0.6502	Remote Similarity	NPD7435	Discontinued
0.65	Remote Similarity	NPD4420	Approved
0.6491	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6625	Approved
0.6484	Remote Similarity	NPD8469	Approved
0.6481	Remote Similarity	NPD8312	Approved
0.6481	Remote Similarity	NPD8313	Approved
0.645	Remote Similarity	NPD7472	Approved
0.6446	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6534	Approved
0.6444	Remote Similarity	NPD6535	Approved
0.6441	Remote Similarity	NPD6843	Phase 3
0.6441	Remote Similarity	NPD6842	Approved
0.6441	Remote Similarity	NPD6841	Approved
0.6438	Remote Similarity	NPD7808	Phase 3
0.6432	Remote Similarity	NPD7199	Phase 2
0.6432	Remote Similarity	NPD6107	Approved
0.6431	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2494	Approved
0.642	Remote Similarity	NPD3452	Approved
0.642	Remote Similarity	NPD2493	Approved
0.642	Remote Similarity	NPD3450	Approved
0.6414	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4582	Approved
0.6408	Remote Similarity	NPD4583	Approved
0.6407	Remote Similarity	NPD7054	Approved
0.6407	Remote Similarity	NPD5844	Phase 1
0.6407	Remote Similarity	NPD4873	Discontinued
0.6405	Remote Similarity	NPD7810	Phase 3
0.6405	Remote Similarity	NPD7811	Phase 3
0.6402	Remote Similarity	NPD6213	Phase 3
0.6402	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6212	Phase 3
0.6397	Remote Similarity	NPD8461	Discontinued
0.6395	Remote Similarity	NPD7240	Approved
0.6393	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6997	Phase 2
0.6389	Remote Similarity	NPD8404	Phase 2
0.6388	Remote Similarity	NPD4666	Phase 3
0.6376	Remote Similarity	NPD5242	Approved
0.6371	Remote Similarity	NPD7906	Approved
0.6367	Remote Similarity	NPD4002	Approved
0.6367	Remote Similarity	NPD4004	Approved
0.6352	Remote Similarity	NPD6297	Approved
0.6352	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD8067	Phase 3
0.6344	Remote Similarity	NPD5709	Phase 3
0.6336	Remote Similarity	NPD6042	Phase 2
0.6336	Remote Similarity	NPD42	Phase 2
0.6327	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7251	Discontinued
0.6322	Remote Similarity	NPD2973	Approved
0.6322	Remote Similarity	NPD2975	Approved
0.6322	Remote Similarity	NPD2974	Approved
0.6318	Remote Similarity	NPD8491	Approved
0.6316	Remote Similarity	NPD6905	Phase 2
0.6316	Remote Similarity	NPD6746	Phase 2
0.6316	Remote Similarity	NPD8161	Suspended
0.6314	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4580	Approved
0.6311	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD6677	Suspended
0.6291	Remote Similarity	NPD7708	Approved
0.6289	Remote Similarity	NPD8366	Approved
0.6282	Remote Similarity	NPD6797	Phase 2
0.6276	Remote Similarity	NPD7861	Discontinued
0.6276	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4040	Phase 1
0.6272	Remote Similarity	NPD6234	Discontinued
0.627	Remote Similarity	NPD7565	Approved
0.6268	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD37	Approved
0.6266	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8492	Approved
0.6261	Remote Similarity	NPD7608	Discontinued
0.626	Remote Similarity	NPD4387	Approved
0.626	Remote Similarity	NPD4386	Approved
0.6259	Remote Similarity	NPD7803	Approved
0.6256	Remote Similarity	NPD4966	Approved
0.6256	Remote Similarity	NPD4965	Approved
0.6256	Remote Similarity	NPD4967	Phase 2
0.6255	Remote Similarity	NPD6034	Phase 2
0.6255	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2490	Approved
0.625	Remote Similarity	NPD2488	Approved
0.625	Remote Similarity	NPD4678	Approved
0.625	Remote Similarity	NPD4675	Approved
0.6245	Remote Similarity	NPD4914	Approved
0.6241	Remote Similarity	NPD8244	Phase 2
0.6239	Remote Similarity	NPD2978	Approved
0.6239	Remote Similarity	NPD2977	Approved
0.6236	Remote Similarity	NPD8367	Approved
0.6229	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7549	Discontinued
0.6226	Remote Similarity	NPD7907	Approved
0.6223	Remote Similarity	NPD6620	Discovery
0.622	Remote Similarity	NPD7047	Phase 3
0.622	Remote Similarity	NPD8149	Discontinued
0.6218	Remote Similarity	NPD7169	Suspended
0.6216	Remote Similarity	NPD7526	Approved
0.6216	Remote Similarity	NPD52	Approved
0.6216	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6166	Phase 2
0.6207	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8285	Discontinued
0.6196	Remote Similarity	NPD7955	Approved
0.6196	Remote Similarity	NPD7956	Approved
0.6195	Remote Similarity	NPD5722	Discontinued
0.6192	Remote Similarity	NPD4663	Approved
0.6192	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5676	Approved
0.6184	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.618	Remote Similarity	NPD7473	Discontinued
0.618	Remote Similarity	NPD5880	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7542	Phase 3
0.6169	Remote Similarity	NPD7680	Approved
0.6167	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7048	Phase 3
0.6163	Remote Similarity	NPD6981	Phase 2
0.6163	Remote Similarity	NPD7805	Phase 3
0.6161	Remote Similarity	NPD3687	Approved

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