NPASS Compound

Structure

NPC473001 OpenBabel07101718332D 106114 0 0 1 0 0 0 0 0999 V2000 5.9442 -0.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2060 0.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9212 0.7066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9442 -2.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 -1.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8874 -6.7905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2475 0.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2743 -4.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3133 -11.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1443 -6.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6795 -7.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3203 0.4176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0355 0.1766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2743 -5.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 -3.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2166 -10.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3127 -11.2810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2258 -9.9816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9955 -8.3938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0256 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9522 1.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1932 -6.4304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7285 -8.0777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1811 -0.5726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8963 -0.8137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 -5.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 -4.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2529 -9.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7822 -10.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0210 -9.3751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9736 -8.1859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5653 0.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9976 1.0462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4034 -9.4128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4955 -7.5278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0581 0.9983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5305 0.5283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2724 -0.8993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0343 -7.7176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8300 -2.1786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6762 -5.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7217 -8.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2743 -1.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5883 -6.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3948 -4.3169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1332 0.0910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 -2.1914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9853 -7.4085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9692 -1.1883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 -5.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2523 -9.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2911 -7.0484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9028 -2.5532 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8102 -5.1914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1918 -7.8190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4844 -1.5150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4083 -0.6914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0056 -5.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 -8.4315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0781 -7.1914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9315 -0.3638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9859 0.0462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3134 -3.3202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1403 -0.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6762 -2.6914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8695 -6.2326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1672 -3.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 -4.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6573 -8.1783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9442 -6.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7540 -0.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 -2.1914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2880 -8.2469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7814 -0.8038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9567 -5.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9903 0.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 0.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9726 -7.1942 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2441 -5.3054 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0044 -2.3691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5403 -7.7089 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4231 -1.6757 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.9442 -5.6914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 -1.1914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2021 -4.5170 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.6762 -3.6914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6902 -8.4548 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 -6.7846 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9333 -0.2738 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.2939 -3.1237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0063 -1.1914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1403 0.3086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7469 -6.7123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1558 -3.3669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9442 -3.6914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0211 -9.1098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8102 -7.1914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4144 -0.1817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 -2.6914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6080 -9.1943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4062 -0.0230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6998 -5.1373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9670 1.1389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2743 0.8086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5422 0.8086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 46 1 0 0 0 0 3 46 1 0 0 0 0 5 47 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 24 1 0 0 0 0 13 25 2 0 0 0 0 14 26 1 0 0 0 0 15 27 2 0 0 0 0 16 28 1 0 0 0 0 17 29 2 0 0 0 0 18 30 1 0 0 0 0 18 34 1 0 0 0 0 19 31 1 0 0 0 0 19 35 1 0 0 0 0 20 32 1 0 0 0 0 20 36 1 0 0 0 0 21 33 1 0 0 0 0 21 37 1 0 0 0 0 22 48 2 0 0 0 0 23 48 1 0 0 0 0 24 49 2 0 0 0 0 25 49 1 0 0 0 0 26 50 2 0 0 0 0 27 50 1 0 0 0 0 28 51 2 0 0 0 0 29 51 1 0 0 0 0 31 60 1 0 0 0 0 34 87 1 0 0 0 0 35 88 1 0 0 0 0 36 89 1 0 0 0 0 37 90 1 0 0 0 0 38 46 1 0 0 0 0 39 48 1 0 0 0 0 40 49 1 0 0 0 0 41 50 1 0 0 0 0 42 51 1 0 0 0 0 43 64 1 0 0 0 0 44 58 2 0 0 0 0 44 78 1 0 0 0 0 45 63 1 0 0 0 0 45 79 1 0 0 0 0 47 4 1 1 0 0 0 47 65 1 0 0 0 0 52 39 1 1 0 0 0 52 66 1 0 0 0 0 52 81 1 0 0 0 0 53 40 1 1 0 0 0 53 67 1 0 0 0 0 53 82 1 0 0 0 0 54 41 1 6 0 0 0 54 68 1 0 0 0 0 54 83 1 0 0 0 0 55 42 1 1 0 0 0 55 73 1 0 0 0 0 55 78 1 0 0 0 0 56 38 1 1 0 0 0 56 74 1 0 0 0 0 56 80 1 0 0 0 0 57 43 1 6 0 0 0 57 77 1 0 0 0 0 57 84 1 0 0 0 0 58 75 1 0 0 0 0 58 85 1 0 0 0 0 59 30 1 1 0 0 0 59 69 1 0 0 0 0 59 87 1 0 0 0 0 60 70 1 6 0 0 0 60 88 1 0 0 0 0 61 32 1 1 0 0 0 61 71 1 0 0 0 0 61 89 1 0 0 0 0 62 33 1 1 0 0 0 62 76 1 0 0 0 0 62 90 1 0 0 0 0 63 80 2 3 0 0 0 63 91 1 0 0 0 0 64 92 2 0 0 0 0 64 93 1 0 0 0 0 65 72 1 1 0 0 0 65 86 1 0 0 0 0 66 79 2 3 0 0 0 66 94 1 0 0 0 0 67 85 2 3 0 0 0 67 95 1 0 0 0 0 68 86 2 3 0 0 0 68 96 1 0 0 0 0 69 81 2 3 0 0 0 69 97 1 0 0 0 0 70 83 2 3 0 0 0 70 98 1 0 0 0 0 71 82 2 3 0 0 0 71 99 1 0 0 0 0 72 84 2 3 0 0 0 72100 1 0 0 0 0 73 87 1 0 0 0 0 73101 2 0 0 0 0 74 90 1 0 0 0 0 74102 2 0 0 0 0 75 88 1 0 0 0 0 75103 2 0 0 0 0 76 89 1 0 0 0 0 76104 2 0 0 0 0 77105 2 0 0 0 0 77106 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1459.72
Volume:	1475.756
LogP:	3.952
LogD:	2.456
LogS:	-2.919
# Rotatable Bonds:	23
TPSA:	418.12
# H-Bond Aceptor:	29
# H-Bond Donor:	11
# Rings:	9
# Heavy Atoms:	29

MedChem Properties

QED Drug-Likeness Score:	0.033
Synthetic Accessibility Score:	7.729
Fsp3:	0.481
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.469
MDCK Permeability:	3.648539131972939e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	55.03426742553711%
Volume Distribution (VD):	0.907
Pgp-substrate:	30.276161193847656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.99
CYP2D6-inhibitor:	0.201
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	1.159
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.995
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.516
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC473001

Natural Product ID:	NPC473001
*Common Name:**	MXQPYQNVFGFAGA-YZQQKWKOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MXQPYQNVFGFAGA-YZQQKWKOSA-N
Standard InCHI:	InChI=1S/C77H97N13O16/c1-5-47(4)65(72(100)84-57(77(105)106)43-64(92)93)86-68(96)54(41-50-26-14-8-15-27-50)83-70(98)60-31-19-35-88(60)75(103)58-44-78-55(42-51-28-16-9-17-29-51)73(101)87-34-18-30-59(87)69(97)81-52(39-48-22-10-6-11-23-48)66(94)79-45-63(91)80-56(38-46(2)3)74(102)90-37-21-33-62(90)76(104)89-36-20-32-61(89)71(99)82-53(67(95)85-58)40-49-24-12-7-13-25-49/h6-17,22-29,44,46-47,52-57,59-62,65,78H,5,18-21,30-43,45H2,1-4H3,(H,79,94)(H,80,91)(H,81,97)(H,82,99)(H,83,98)(H,84,100)(H,85,95)(H,86,96)(H,92,93)(H,105,106)/b58-44-/t47-,52-,53-,54-,55-,56-,57-,59-,60-,61-,62-,65-/m0/s1
SMILES:	CCC(C)C(C(=O)NC(CC(=O)O)C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)C2CCCN2C(=O)C3=CNC(C(=O)N4CCCC4C(=O)NC(C(=O)NCC(=O)NC(C(=O)N5CCCC5C(=O)N6CCCC6C(=O)NC(C(=O)N3)CC7=CC=CC=C7)CC(C)C)CC8=CC=CC=C8)CC9=CC=CC=C9
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597657
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0003297] Organic Polymers [CHEMONTID:0003298] Polypeptides

*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
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26213786]
NPO16915	Callyspongia aerizusa	Species	Callyspongiidae	Eukaryota	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
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[543754]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	10000.0	nM	PMID[543754]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	100000.0	nM	PMID[543754]

☑ 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 NPC473001 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	269
0.1-0.2	1436
0.2-0.3	9161
0.3-0.4	22896
0.4-0.5	6711
0.5-0.6	1735
0.6-0.7	430
0.7-0.8	49
0.8-0.85	3
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9255	High Similarity	NPC469904
0.9241	High Similarity	NPC469902
0.9241	High Similarity	NPC473003
0.8987	High Similarity	NPC469903
0.8924	High Similarity	NPC473002
0.875	High Similarity	NPC469900
0.865	High Similarity	NPC469901
0.8589	High Similarity	NPC469898
0.8563	High Similarity	NPC473000
0.7865	Intermediate Similarity	NPC472999
0.7765	Intermediate Similarity	NPC324850
0.7722	Intermediate Similarity	NPC255447
0.7658	Intermediate Similarity	NPC200589
0.7595	Intermediate Similarity	NPC473322
0.7557	Intermediate Similarity	NPC141957
0.7444	Intermediate Similarity	NPC477462
0.7439	Intermediate Similarity	NPC132636
0.7425	Intermediate Similarity	NPC315266
0.7396	Intermediate Similarity	NPC240848
0.7394	Intermediate Similarity	NPC276430
0.7375	Intermediate Similarity	NPC111428
0.736	Intermediate Similarity	NPC328649
0.733	Intermediate Similarity	NPC241794
0.7326	Intermediate Similarity	NPC122590
0.7321	Intermediate Similarity	NPC209509
0.7305	Intermediate Similarity	NPC77905
0.7284	Intermediate Similarity	NPC130309
0.7278	Intermediate Similarity	NPC262077
0.7262	Intermediate Similarity	NPC476978
0.7256	Intermediate Similarity	NPC141050
0.7253	Intermediate Similarity	NPC136797
0.7219	Intermediate Similarity	NPC307396
0.7219	Intermediate Similarity	NPC316008
0.7219	Intermediate Similarity	NPC313867
0.7209	Intermediate Similarity	NPC7817
0.7209	Intermediate Similarity	NPC475168
0.7176	Intermediate Similarity	NPC314358
0.716	Intermediate Similarity	NPC315283
0.716	Intermediate Similarity	NPC314388
0.7159	Intermediate Similarity	NPC297145
0.7159	Intermediate Similarity	NPC197743
0.7152	Intermediate Similarity	NPC71684
0.7151	Intermediate Similarity	NPC2501
0.7111	Intermediate Similarity	NPC61004
0.7101	Intermediate Similarity	NPC161069
0.7091	Intermediate Similarity	NPC287401
0.7089	Intermediate Similarity	NPC200964
0.7086	Intermediate Similarity	NPC470902
0.7072	Intermediate Similarity	NPC302597
0.7059	Intermediate Similarity	NPC52748
0.7056	Intermediate Similarity	NPC189116
0.7041	Intermediate Similarity	NPC263493
0.7041	Intermediate Similarity	NPC269398
0.7024	Intermediate Similarity	NPC98424
0.7024	Intermediate Similarity	NPC92784
0.7024	Intermediate Similarity	NPC476133
0.7024	Intermediate Similarity	NPC470884
0.7024	Intermediate Similarity	NPC178662
0.7018	Intermediate Similarity	NPC322878
0.6973	Remote Similarity	NPC326407
0.6973	Remote Similarity	NPC317725
0.6964	Remote Similarity	NPC471264
0.6964	Remote Similarity	NPC471265
0.6962	Remote Similarity	NPC470546
0.6936	Remote Similarity	NPC138775
0.6935	Remote Similarity	NPC196243
0.6932	Remote Similarity	NPC261934
0.6932	Remote Similarity	NPC5194
0.6932	Remote Similarity	NPC202198
0.6927	Remote Similarity	NPC24617
0.6919	Remote Similarity	NPC5620
0.6899	Remote Similarity	NPC470545
0.6897	Remote Similarity	NPC471820
0.6897	Remote Similarity	NPC471821
0.6889	Remote Similarity	NPC471527
0.6889	Remote Similarity	NPC114806
0.6878	Remote Similarity	NPC75634
0.6875	Remote Similarity	NPC233702
0.6871	Remote Similarity	NPC101719
0.6868	Remote Similarity	NPC223207
0.6852	Remote Similarity	NPC6975
0.6839	Remote Similarity	NPC311658
0.6836	Remote Similarity	NPC56685
0.6836	Remote Similarity	NPC473341
0.6835	Remote Similarity	NPC470544
0.6831	Remote Similarity	NPC471771
0.6831	Remote Similarity	NPC304074
0.6831	Remote Similarity	NPC290755
0.6829	Remote Similarity	NPC477937
0.6828	Remote Similarity	NPC475532
0.6824	Remote Similarity	NPC89489
0.6813	Remote Similarity	NPC471053
0.6813	Remote Similarity	NPC471051
0.6813	Remote Similarity	NPC471052
0.6811	Remote Similarity	NPC274198
0.6811	Remote Similarity	NPC198254
0.681	Remote Similarity	NPC222466
0.681	Remote Similarity	NPC22746
0.6807	Remote Similarity	NPC300315
0.6791	Remote Similarity	NPC165285
0.6784	Remote Similarity	NPC163392
0.6784	Remote Similarity	NPC239762
0.678	Remote Similarity	NPC300443
0.6776	Remote Similarity	NPC63931
0.6761	Remote Similarity	NPC129666
0.674	Remote Similarity	NPC62104
0.674	Remote Similarity	NPC1390
0.6738	Remote Similarity	NPC242269
0.673	Remote Similarity	NPC239357
0.6728	Remote Similarity	NPC202521
0.672	Remote Similarity	NPC276506
0.6718	Remote Similarity	NPC61332
0.6718	Remote Similarity	NPC240130
0.6717	Remote Similarity	NPC329295
0.6716	Remote Similarity	NPC54420
0.6705	Remote Similarity	NPC139326
0.6705	Remote Similarity	NPC197682
0.6705	Remote Similarity	NPC105717
0.6703	Remote Similarity	NPC469243
0.6702	Remote Similarity	NPC317362
0.6702	Remote Similarity	NPC318930
0.6687	Remote Similarity	NPC319766
0.6686	Remote Similarity	NPC314114
0.6686	Remote Similarity	NPC476259
0.6684	Remote Similarity	NPC194671
0.6684	Remote Similarity	NPC269750
0.6667	Remote Similarity	NPC254798
0.6667	Remote Similarity	NPC129486
0.6667	Remote Similarity	NPC476990
0.6667	Remote Similarity	NPC127741
0.665	Remote Similarity	NPC162860
0.6649	Remote Similarity	NPC15068
0.6649	Remote Similarity	NPC137627
0.6648	Remote Similarity	NPC16188
0.6648	Remote Similarity	NPC225648
0.6648	Remote Similarity	NPC329761
0.6647	Remote Similarity	NPC168113
0.6646	Remote Similarity	NPC46427
0.6636	Remote Similarity	NPC478028
0.6634	Remote Similarity	NPC472538
0.6632	Remote Similarity	NPC294951
0.6625	Remote Similarity	NPC285926
0.6625	Remote Similarity	NPC14672
0.6625	Remote Similarity	NPC315276
0.6614	Remote Similarity	NPC17698
0.6614	Remote Similarity	NPC279871
0.6613	Remote Similarity	NPC63040
0.6612	Remote Similarity	NPC475544
0.6609	Remote Similarity	NPC176226
0.6608	Remote Similarity	NPC314835
0.6596	Remote Similarity	NPC89831
0.6595	Remote Similarity	NPC22883
0.6595	Remote Similarity	NPC210377
0.6595	Remote Similarity	NPC217804
0.6595	Remote Similarity	NPC5719
0.6592	Remote Similarity	NPC162104
0.6588	Remote Similarity	NPC238945
0.6585	Remote Similarity	NPC252878
0.6585	Remote Similarity	NPC225400
0.6583	Remote Similarity	NPC477632
0.6583	Remote Similarity	NPC477638
0.6582	Remote Similarity	NPC474584
0.6577	Remote Similarity	NPC478029
0.6567	Remote Similarity	NPC171317
0.6566	Remote Similarity	NPC47667
0.6561	Remote Similarity	NPC248670
0.6561	Remote Similarity	NPC306804
0.6556	Remote Similarity	NPC262166
0.6556	Remote Similarity	NPC286551
0.6554	Remote Similarity	NPC145113
0.6553	Remote Similarity	NPC470786
0.6553	Remote Similarity	NPC471155
0.655	Remote Similarity	NPC248283
0.6548	Remote Similarity	NPC163961
0.6548	Remote Similarity	NPC473305
0.6545	Remote Similarity	NPC175726
0.6545	Remote Similarity	NPC474082
0.6543	Remote Similarity	NPC475123
0.6543	Remote Similarity	NPC40234
0.6543	Remote Similarity	NPC475204
0.6531	Remote Similarity	NPC94862
0.6526	Remote Similarity	NPC471165
0.6526	Remote Similarity	NPC158277
0.6526	Remote Similarity	NPC159767
0.6526	Remote Similarity	NPC26108
0.6526	Remote Similarity	NPC155506
0.6522	Remote Similarity	NPC276085
0.6522	Remote Similarity	NPC270241
0.6522	Remote Similarity	NPC475259
0.6522	Remote Similarity	NPC471945
0.6522	Remote Similarity	NPC471950
0.6522	Remote Similarity	NPC470491
0.6519	Remote Similarity	NPC329011
0.6514	Remote Similarity	NPC468984
0.651	Remote Similarity	NPC45037
0.6509	Remote Similarity	NPC471197
0.6508	Remote Similarity	NPC230611
0.65	Remote Similarity	NPC33742
0.6493	Remote Similarity	NPC478157
0.6492	Remote Similarity	NPC50016

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 NPC473001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	437
0.2-0.3	893
0.3-0.4	2695
0.4-0.5	3906
0.5-0.6	935
0.6-0.7	120
0.7-0.8	6
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
0.7515	Intermediate Similarity	NPD8076	Discontinued
0.7421	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8240	Discontinued
0.7333	Intermediate Similarity	NPD6901	Phase 3
0.7317	Intermediate Similarity	NPD8643	Discontinued
0.7308	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7728	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5263	Approved
0.7222	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3071	Approved
0.717	Intermediate Similarity	NPD3072	Approved
0.717	Intermediate Similarity	NPD3073	Approved
0.7117	Intermediate Similarity	NPD4676	Approved
0.7107	Intermediate Similarity	NPD4761	Approved
0.7107	Intermediate Similarity	NPD4762	Approved
0.7101	Intermediate Similarity	NPD7720	Phase 2
0.7066	Intermediate Similarity	NPD6073	Approved
0.7052	Intermediate Similarity	NPD6631	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8416	Discontinued
0.7025	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5725	Approved
0.6954	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4177	Approved
0.6951	Remote Similarity	NPD4175	Approved
0.6927	Remote Similarity	NPD8630	Approved
0.6914	Remote Similarity	NPD4677	Discontinued
0.6894	Remote Similarity	NPD4706	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3040	Approved
0.6845	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8323	Discontinued
0.6839	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5581	Approved
0.6824	Remote Similarity	NPD4126	Approved
0.6798	Remote Similarity	NPD8315	Phase 1
0.6786	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8172	Phase 2
0.6765	Remote Similarity	NPD8173	Phase 2
0.6725	Remote Similarity	NPD6852	Discontinued
0.6707	Remote Similarity	NPD4125	Approved
0.6707	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5747	Discontinued
0.6667	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8303	Discontinued
0.6647	Remote Similarity	NPD6623	Phase 3
0.6647	Remote Similarity	NPD5323	Approved
0.6647	Remote Similarity	NPD4153	Approved
0.6646	Remote Similarity	NPD2584	Suspended
0.663	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5264	Approved
0.6629	Remote Similarity	NPD5265	Approved
0.6628	Remote Similarity	NPD6294	Approved
0.6628	Remote Similarity	NPD6295	Approved
0.6608	Remote Similarity	NPD3908	Approved
0.6598	Remote Similarity	NPD6557	Phase 2
0.6592	Remote Similarity	NPD7613	Discontinued
0.6591	Remote Similarity	NPD1967	Approved
0.6591	Remote Similarity	NPD1968	Approved
0.659	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4151	Approved
0.6573	Remote Similarity	NPD6088	Approved
0.6545	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8351	Phase 2
0.6534	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5024	Approved
0.6532	Remote Similarity	NPD4214	Discontinued
0.6531	Remote Similarity	NPD7683	Discontinued
0.6529	Remote Similarity	NPD1330	Phase 2
0.6529	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5299	Approved
0.6522	Remote Similarity	NPD7599	Phase 2
0.6514	Remote Similarity	NPD2087	Approved
0.6514	Remote Similarity	NPD2088	Approved
0.6512	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1348	Approved
0.6459	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5296	Approved
0.645	Remote Similarity	NPD5759	Approved
0.644	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3519	Discontinued
0.6425	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7771	Discontinued
0.6394	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD8322	Phase 2
0.6392	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5367	Discontinued
0.6364	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5942	Approved
0.6354	Remote Similarity	NPD4432	Discontinued
0.6354	Remote Similarity	NPD5941	Approved
0.6353	Remote Similarity	NPD7828	Discontinued
0.6338	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7970	Approved
0.6337	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3510	Approved
0.6333	Remote Similarity	NPD3509	Approved
0.6332	Remote Similarity	NPD5852	Approved
0.6332	Remote Similarity	NPD5851	Approved
0.6331	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD2022	Approved
0.6324	Remote Similarity	NPD7105	Phase 1
0.6319	Remote Similarity	NPD5748	Phase 2
0.6319	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7600	Phase 2
0.6302	Remote Similarity	NPD7965	Phase 2
0.6302	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD2013	Approved
0.6298	Remote Similarity	NPD8098	Approved
0.6298	Remote Similarity	NPD2014	Approved
0.6298	Remote Similarity	NPD2016	Approved
0.6296	Remote Similarity	NPD747	Discontinued
0.629	Remote Similarity	NPD8019	Approved
0.6286	Remote Similarity	NPD8125	Discontinued
0.6284	Remote Similarity	NPD7523	Phase 3
0.6283	Remote Similarity	NPD7795	Phase 2
0.6279	Remote Similarity	NPD4794	Discontinued
0.6272	Remote Similarity	NPD6792	Phase 3
0.625	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7789	Approved
0.625	Remote Similarity	NPD7791	Approved
0.625	Remote Similarity	NPD7953	Approved
0.625	Remote Similarity	NPD7790	Approved
0.625	Remote Similarity	NPD7950	Approved
0.625	Remote Similarity	NPD7952	Approved
0.625	Remote Similarity	NPD7951	Approved
0.625	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD951	Approved
0.623	Remote Similarity	NPD5230	Approved
0.623	Remote Similarity	NPD6304	Approved
0.623	Remote Similarity	NPD5229	Approved
0.623	Remote Similarity	NPD6303	Approved
0.6229	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8114	Approved
0.622	Remote Similarity	NPD8115	Approved
0.6219	Remote Similarity	NPD7617	Discontinued
0.6218	Remote Similarity	NPD8124	Phase 3
0.6218	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD7781	Approved
0.6216	Remote Similarity	NPD7780	Approved
0.6209	Remote Similarity	NPD5613	Approved
0.6209	Remote Similarity	NPD3987	Approved
0.6209	Remote Similarity	NPD3988	Approved
0.6209	Remote Similarity	NPD5614	Approved
0.6207	Remote Similarity	NPD941	Approved
0.6204	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7011	Discontinued
0.6203	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD2437	Approved
0.6201	Remote Similarity	NPD2436	Approved
0.6201	Remote Similarity	NPD6681	Discovery
0.6198	Remote Similarity	NPD4652	Approved
0.6197	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD5004	Approved
0.6188	Remote Similarity	NPD5076	Approved
0.6188	Remote Similarity	NPD5077	Approved
0.6188	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2051	Approved
0.6185	Remote Similarity	NPD2043	Approved
0.6185	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2044	Approved
0.6185	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD2046	Approved
0.6185	Remote Similarity	NPD2045	Approved
0.6185	Remote Similarity	NPD2047	Approved
0.6185	Remote Similarity	NPD2048	Approved
0.6185	Remote Similarity	NPD21	Approved
0.618	Remote Similarity	NPD7512	Approved
0.618	Remote Similarity	NPD7511	Approved
0.6175	Remote Similarity	NPD4682	Phase 2
0.617	Remote Similarity	NPD4567	Approved
0.617	Remote Similarity	NPD4557	Approved
0.617	Remote Similarity	NPD4566	Approved
0.6168	Remote Similarity	NPD8097	Phase 3
0.6168	Remote Similarity	NPD7605	Discovery
0.6168	Remote Similarity	NPD8096	Phase 3
0.6167	Remote Similarity	NPD3508	Approved
0.6166	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4646	Approved
0.6162	Remote Similarity	NPD4647	Approved
0.6162	Remote Similarity	NPD4648	Approved
0.6158	Remote Similarity	NPD6665	Discontinued
0.6158	Remote Similarity	NPD7569	Approved
0.6158	Remote Similarity	NPD3790	Phase 2
0.6158	Remote Similarity	NPD7570	Approved
0.6154	Remote Similarity	NPD7817	Phase 1
0.6145	Remote Similarity	NPD3625	Discontinued
0.6142	Remote Similarity	NPD3989	Phase 3

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