NPASS Compound

Structure

NPC231712 OpenBabel07101718322D 68 79 0 0 1 0 0 0 0 0999 V2000 -2.1150 -3.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4386 -4.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1704 -5.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2894 -4.7136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5191 -1.8071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0798 -0.2604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7583 -0.9184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9572 -2.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5510 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8746 -5.1391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8667 -6.5656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9856 -5.3596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4120 -2.1308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9728 -0.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5879 -1.3810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7868 -2.8178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1294 -2.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0674 -2.7564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 0.0643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5927 -0.0162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5271 -3.2153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 -4.1811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6364 1.1234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4622 0.7060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0588 -3.5043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3818 -4.9935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3530 -0.8719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9430 -1.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9308 -5.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7743 -6.2856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1388 -1.5194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6021 -2.3307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1428 -2.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0674 -3.7062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7012 0.9573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2014 0.6171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5002 -1.7779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 -2.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9889 -0.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3416 -0.7170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8980 -2.8676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7125 -3.7062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2478 0.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9319 0.1836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1869 -1.9759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5967 -2.4094 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8845 -2.1489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7125 -2.7564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9241 -0.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3945 -0.6460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8159 -1.3602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8767 -1.5018 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6733 -1.0803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7484 -1.3423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4600 -0.5481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1134 -0.9430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3668 -5.7970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4705 -6.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0318 -1.8431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4317 -2.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9741 -3.3038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7551 -4.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0898 1.6841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7127 1.4176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0845 -3.3578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5351 -4.1811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1971 0.3646 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 1 9 1 0 0 0 0 1 25 2 0 0 0 0 2 10 2 0 0 0 0 2 25 1 0 0 0 0 3 11 1 0 0 0 0 3 26 2 0 0 0 0 4 12 2 0 0 0 0 4 26 1 0 0 0 0 5 13 1 0 0 0 0 5 27 2 0 0 0 0 6 14 2 0 0 0 0 6 27 1 0 0 0 0 7 15 1 0 0 0 0 7 28 2 0 0 0 0 8 16 2 0 0 0 0 8 28 1 0 0 0 0 9 29 2 0 0 0 0 10 29 1 0 0 0 0 11 30 2 0 0 0 0 12 30 1 0 0 0 0 13 31 2 0 0 0 0 14 31 1 0 0 0 0 15 32 2 0 0 0 0 16 32 1 0 0 0 0 17 33 2 0 0 0 0 17 37 1 0 0 0 0 18 34 2 0 0 0 0 18 38 1 0 0 0 0 19 35 2 0 0 0 0 19 39 1 0 0 0 0 20 36 2 0 0 0 0 20 40 1 0 0 0 0 21 33 1 0 0 0 0 21 41 2 0 0 0 0 22 34 1 0 0 0 0 22 42 2 0 0 0 0 23 35 1 0 0 0 0 23 43 2 0 0 0 0 24 36 1 0 0 0 0 24 44 2 0 0 0 0 29 57 1 0 0 0 0 30 58 1 0 0 0 0 31 59 1 0 0 0 0 32 60 1 0 0 0 0 33 61 1 0 0 0 0 34 62 1 0 0 0 0 35 63 1 0 0 0 0 36 64 1 0 0 0 0 37 47 2 0 0 0 0 38 48 2 0 0 0 0 39 49 2 0 0 0 0 40 50 2 0 0 0 0 41 47 1 0 0 0 0 41 65 1 0 0 0 0 42 48 1 0 0 0 0 42 66 1 0 0 0 0 43 49 1 0 0 0 0 43 67 1 0 0 0 0 44 50 1 0 0 0 0 44 68 1 0 0 0 0 45 25 1 1 0 0 0 45 47 1 0 0 0 0 45 51 1 0 0 0 0 46 26 1 6 0 0 0 46 48 1 0 0 0 0 46 52 1 0 0 0 0 49 53 1 0 0 0 0 50 54 1 0 0 0 0 51 39 1 6 0 0 0 51 52 1 0 0 0 0 52 40 1 6 0 0 0 53 37 1 1 0 0 0 53 55 1 0 0 0 0 54 38 1 6 0 0 0 54 56 1 0 0 0 0 55 27 1 6 0 0 0 55 67 1 0 0 0 0 56 28 1 1 0 0 0 56 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	906.27
Volume:	916.662
LogP:	8.356
LogD:	4.279
LogS:	-4.334
# Rotatable Bonds:	5
TPSA:	220.76
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	12
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.078
Synthetic Accessibility Score:	5.117
Fsp3:	0.143
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:	-6.527
MDCK Permeability:	3.849762833851855e-06
Pgp-inhibitor:	0.447
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	94.1921615600586%
Volume Distribution (VD):	0.699
Pgp-substrate:	7.023526668548584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.708
CYP2C19-inhibitor:	0.962
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.785
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.205
CYP3A4-substrate:	0.706

ADMET: Excretion

Clearance (CL):	7.439
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.948
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.904
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC231712

Natural Product ID:	NPC231712
*Common Name:**	Isohopeaphenol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YQQUILZPDYJDQJ-CMUHVXPYSA-N
Standard InCHI:	InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46-,51-,52+,53+,54+,55-,56-/m0/s1
SMILES:	c1cc(ccc1[C@H]1c2c(cc(cc2O)O)[C@@H]2c3c(cc(cc3O[C@H]2c2ccc(cc2)O)O)[C@@H]1[C@@H]1c2cc(cc3c2[C@@H](c2cc(cc(c2[C@@H]1c1ccc(cc1)O)O)O)[C@H](c1ccc(cc1)O)O3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510147
PubChem CID:	11967401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO32506	Vatica oblongifolia	Species	Dipterocarpaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[12444676]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[513258]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	100.0	ug.mL-1	PMID[513258]

☑ 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 NPC231712 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	498
0.1-0.2	1672
0.2-0.3	4280
0.3-0.4	12302
0.4-0.5	6286
0.5-0.6	4707
0.6-0.7	8751
0.7-0.8	3576
0.8-0.85	446
0.85-0.9	121
0.9-0.95	37
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224921
1.0	High Similarity	NPC237546
1.0	High Similarity	NPC242774
0.9716	High Similarity	NPC111134
0.9574	High Similarity	NPC149633
0.9448	High Similarity	NPC105073
0.9448	High Similarity	NPC224528
0.9448	High Similarity	NPC233886
0.9444	High Similarity	NPC122980
0.9444	High Similarity	NPC177172
0.9444	High Similarity	NPC148516
0.9444	High Similarity	NPC107862
0.9444	High Similarity	NPC180605
0.9441	High Similarity	NPC6702
0.9441	High Similarity	NPC133209
0.9441	High Similarity	NPC112819
0.9371	High Similarity	NPC176804
0.9371	High Similarity	NPC71686
0.9247	High Similarity	NPC218801
0.9236	High Similarity	NPC14468
0.922	High Similarity	NPC213607
0.922	High Similarity	NPC182509
0.922	High Similarity	NPC174787
0.9209	High Similarity	NPC15109
0.9209	High Similarity	NPC11727
0.9184	High Similarity	NPC157081
0.9145	High Similarity	NPC48880
0.9	High Similarity	NPC157333
0.8993	High Similarity	NPC473018
0.8993	High Similarity	NPC120633
0.894	High Similarity	NPC202104
0.8936	High Similarity	NPC125579
0.8873	High Similarity	NPC141717
0.8836	High Similarity	NPC15659
0.8836	High Similarity	NPC304894
0.8811	High Similarity	NPC470308
0.8811	High Similarity	NPC470307
0.8786	High Similarity	NPC473309
0.8767	High Similarity	NPC173203
0.8767	High Similarity	NPC163508
0.8742	High Similarity	NPC476391
0.8742	High Similarity	NPC233467
0.8741	High Similarity	NPC471522
0.8732	High Similarity	NPC476616
0.8732	High Similarity	NPC476615
0.8732	High Similarity	NPC476617
0.8725	High Similarity	NPC329836
0.8675	High Similarity	NPC324517
0.8675	High Similarity	NPC321972
0.8675	High Similarity	NPC329343
0.8643	High Similarity	NPC471518
0.8643	High Similarity	NPC471519
0.8562	High Similarity	NPC273623
0.8543	High Similarity	NPC473266
0.8543	High Similarity	NPC470098
0.8543	High Similarity	NPC470826
0.8535	High Similarity	NPC90822
0.8533	High Similarity	NPC328567
0.8533	High Similarity	NPC327412
0.8533	High Similarity	NPC320671
0.8533	High Similarity	NPC320970
0.8531	High Similarity	NPC469610
0.8521	High Similarity	NPC471517
0.8521	High Similarity	NPC8899
0.8497	Intermediate Similarity	NPC59692
0.8481	Intermediate Similarity	NPC261896
0.8477	Intermediate Similarity	NPC227516
0.8477	Intermediate Similarity	NPC20757
0.8472	Intermediate Similarity	NPC473107
0.8467	Intermediate Similarity	NPC317053
0.8467	Intermediate Similarity	NPC324492
0.8462	Intermediate Similarity	NPC469611
0.8451	Intermediate Similarity	NPC254000
0.8425	Intermediate Similarity	NPC71465
0.8425	Intermediate Similarity	NPC472646
0.8421	Intermediate Similarity	NPC476969
0.8421	Intermediate Similarity	NPC321657
0.8421	Intermediate Similarity	NPC318373
0.8414	Intermediate Similarity	NPC258780
0.8414	Intermediate Similarity	NPC37410
0.8403	Intermediate Similarity	NPC473665
0.8392	Intermediate Similarity	NPC237424
0.8392	Intermediate Similarity	NPC238168
0.8378	Intermediate Similarity	NPC100482
0.8378	Intermediate Similarity	NPC277331
0.8377	Intermediate Similarity	NPC279406
0.8377	Intermediate Similarity	NPC226809
0.8366	Intermediate Similarity	NPC477612
0.8357	Intermediate Similarity	NPC113495
0.8356	Intermediate Similarity	NPC206525
0.8356	Intermediate Similarity	NPC191462
0.8356	Intermediate Similarity	NPC472648
0.8356	Intermediate Similarity	NPC170328
0.8356	Intermediate Similarity	NPC133463
0.8356	Intermediate Similarity	NPC472649
0.8356	Intermediate Similarity	NPC472647
0.8333	Intermediate Similarity	NPC475492
0.8333	Intermediate Similarity	NPC114119
0.8333	Intermediate Similarity	NPC470097
0.8333	Intermediate Similarity	NPC471415
0.8323	Intermediate Similarity	NPC224161
0.8311	Intermediate Similarity	NPC472090
0.8311	Intermediate Similarity	NPC472092
0.8311	Intermediate Similarity	NPC472091
0.831	Intermediate Similarity	NPC47283
0.831	Intermediate Similarity	NPC39064
0.8298	Intermediate Similarity	NPC471215
0.8298	Intermediate Similarity	NPC262573
0.8289	Intermediate Similarity	NPC170103
0.8289	Intermediate Similarity	NPC153182
0.8289	Intermediate Similarity	NPC82917
0.8289	Intermediate Similarity	NPC174251
0.8289	Intermediate Similarity	NPC108811
0.8289	Intermediate Similarity	NPC202742
0.8289	Intermediate Similarity	NPC18185
0.8289	Intermediate Similarity	NPC70409
0.8289	Intermediate Similarity	NPC204770
0.8289	Intermediate Similarity	NPC262911
0.8289	Intermediate Similarity	NPC294558
0.8289	Intermediate Similarity	NPC263940
0.8289	Intermediate Similarity	NPC236202
0.8289	Intermediate Similarity	NPC58190
0.828	Intermediate Similarity	NPC55463
0.828	Intermediate Similarity	NPC166116
0.8278	Intermediate Similarity	NPC181615
0.8269	Intermediate Similarity	NPC46335
0.8264	Intermediate Similarity	NPC129784
0.8264	Intermediate Similarity	NPC181497
0.8264	Intermediate Similarity	NPC280653
0.8264	Intermediate Similarity	NPC236014
0.8264	Intermediate Similarity	NPC150011
0.8264	Intermediate Similarity	NPC300875
0.8264	Intermediate Similarity	NPC282508
0.8264	Intermediate Similarity	NPC17343
0.8264	Intermediate Similarity	NPC207892
0.8264	Intermediate Similarity	NPC118114
0.8264	Intermediate Similarity	NPC271945
0.8264	Intermediate Similarity	NPC472590
0.8264	Intermediate Similarity	NPC196765
0.8264	Intermediate Similarity	NPC12875
0.8264	Intermediate Similarity	NPC228369
0.8264	Intermediate Similarity	NPC129106
0.8264	Intermediate Similarity	NPC476166
0.8264	Intermediate Similarity	NPC268917
0.8264	Intermediate Similarity	NPC206224
0.8264	Intermediate Similarity	NPC164574
0.8255	Intermediate Similarity	NPC178054
0.8235	Intermediate Similarity	NPC281549
0.8224	Intermediate Similarity	NPC274454
0.8224	Intermediate Similarity	NPC260397
0.8224	Intermediate Similarity	NPC96576
0.8224	Intermediate Similarity	NPC215678
0.8219	Intermediate Similarity	NPC296915
0.8219	Intermediate Similarity	NPC115335
0.8219	Intermediate Similarity	NPC198154
0.8219	Intermediate Similarity	NPC225696
0.8219	Intermediate Similarity	NPC223008
0.8219	Intermediate Similarity	NPC97834
0.8212	Intermediate Similarity	NPC171932
0.8212	Intermediate Similarity	NPC28440
0.8207	Intermediate Similarity	NPC13005
0.82	Intermediate Similarity	NPC472088
0.82	Intermediate Similarity	NPC472087
0.8194	Intermediate Similarity	NPC471403
0.8194	Intermediate Similarity	NPC470225
0.8194	Intermediate Similarity	NPC27187
0.8188	Intermediate Similarity	NPC262189
0.8188	Intermediate Similarity	NPC22317
0.8182	Intermediate Similarity	NPC211561
0.8182	Intermediate Similarity	NPC295573
0.8182	Intermediate Similarity	NPC470208
0.8176	Intermediate Similarity	NPC474687
0.817	Intermediate Similarity	NPC262297
0.8169	Intermediate Similarity	NPC283049
0.8169	Intermediate Similarity	NPC50315
0.8169	Intermediate Similarity	NPC230479
0.8169	Intermediate Similarity	NPC26879
0.8138	Intermediate Similarity	NPC162801
0.8133	Intermediate Similarity	NPC470372
0.8133	Intermediate Similarity	NPC472089
0.8129	Intermediate Similarity	NPC205501
0.8129	Intermediate Similarity	NPC162976
0.8129	Intermediate Similarity	NPC118000
0.8125	Intermediate Similarity	NPC93962
0.8125	Intermediate Similarity	NPC1253
0.8125	Intermediate Similarity	NPC100936
0.8121	Intermediate Similarity	NPC260842
0.8121	Intermediate Similarity	NPC55947
0.8113	Intermediate Similarity	NPC4809
0.8113	Intermediate Similarity	NPC125495
0.8113	Intermediate Similarity	NPC73517
0.8113	Intermediate Similarity	NPC470827
0.8113	Intermediate Similarity	NPC147743
0.8108	Intermediate Similarity	NPC3049
0.8108	Intermediate Similarity	NPC234952
0.8105	Intermediate Similarity	NPC102280
0.8105	Intermediate Similarity	NPC248053
0.8105	Intermediate Similarity	NPC155564
0.8095	Intermediate Similarity	NPC256307
0.8095	Intermediate Similarity	NPC66840

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 NPC231712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	944
0.2-0.3	1698
0.3-0.4	2767
0.4-0.5	1694
0.5-0.6	1014
0.6-0.7	553
0.7-0.8	70
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD4908	Phase 1
0.8322	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1610	Phase 2
0.7862	Intermediate Similarity	NPD2861	Phase 2
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7755	Intermediate Similarity	NPD4625	Phase 3
0.7718	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1613	Approved
0.7586	Intermediate Similarity	NPD4749	Approved
0.7584	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7447	Phase 1
0.753	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7213	Phase 3
0.7468	Intermediate Similarity	NPD7212	Phase 2
0.7425	Intermediate Similarity	NPD7199	Phase 2
0.7412	Intermediate Similarity	NPD7228	Approved
0.741	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD3027	Phase 3
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.7394	Intermediate Similarity	NPD4966	Approved
0.7394	Intermediate Similarity	NPD4965	Approved
0.7394	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD7466	Approved
0.7389	Intermediate Similarity	NPD3892	Phase 2
0.7372	Intermediate Similarity	NPD7037	Approved
0.7337	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5735	Approved
0.7315	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD3750	Approved
0.7273	Intermediate Similarity	NPD7819	Suspended
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5327	Phase 3
0.723	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD37	Approved
0.7193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD8455	Phase 2
0.7161	Intermediate Similarity	NPD6353	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7119	Intermediate Similarity	NPD8054	Approved
0.7119	Intermediate Similarity	NPD8053	Approved
0.7097	Intermediate Similarity	NPD5124	Phase 1
0.7097	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6166	Phase 2
0.7089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6584	Phase 3
0.7067	Intermediate Similarity	NPD6696	Suspended
0.7062	Intermediate Similarity	NPD8313	Approved
0.7062	Intermediate Similarity	NPD8312	Approved
0.7045	Intermediate Similarity	NPD7240	Approved
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7032	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5762	Approved
0.6981	Remote Similarity	NPD5763	Approved
0.698	Remote Similarity	NPD422	Phase 1
0.6971	Remote Similarity	NPD5844	Phase 1
0.6971	Remote Similarity	NPD8156	Discontinued
0.6966	Remote Similarity	NPD6671	Approved
0.6964	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3748	Approved
0.6957	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8651	Approved
0.6946	Remote Similarity	NPD7411	Suspended
0.6943	Remote Similarity	NPD4097	Suspended
0.6928	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3018	Phase 2
0.6914	Remote Similarity	NPD8099	Discontinued
0.6914	Remote Similarity	NPD8251	Approved
0.6914	Remote Similarity	NPD8252	Approved
0.691	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1934	Approved
0.6903	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7119	Phase 2
0.6899	Remote Similarity	NPD7097	Phase 1
0.689	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6582	Phase 2
0.6887	Remote Similarity	NPD6583	Phase 3
0.6886	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD7843	Approved
0.6857	Remote Similarity	NPD7473	Discontinued
0.6855	Remote Similarity	NPD1510	Phase 2
0.6849	Remote Similarity	NPD7157	Approved
0.6845	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7075	Discontinued
0.6842	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7074	Phase 3
0.6835	Remote Similarity	NPD2157	Approved
0.6832	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7390	Discontinued
0.6818	Remote Similarity	NPD3818	Discontinued
0.6815	Remote Similarity	NPD2238	Phase 2
0.6815	Remote Similarity	NPD3620	Phase 2
0.6815	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2796	Approved
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6798	Discontinued
0.6789	Remote Similarity	NPD7680	Approved
0.6788	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3882	Suspended
0.6783	Remote Similarity	NPD4750	Phase 3
0.6782	Remote Similarity	NPD6232	Discontinued
0.678	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7054	Approved
0.6776	Remote Similarity	NPD2983	Phase 2
0.6776	Remote Similarity	NPD2982	Phase 2
0.6766	Remote Similarity	NPD1653	Approved
0.6763	Remote Similarity	NPD5494	Approved
0.676	Remote Similarity	NPD6559	Discontinued
0.6755	Remote Similarity	NPD1091	Approved
0.6753	Remote Similarity	NPD4624	Approved
0.675	Remote Similarity	NPD5588	Approved
0.675	Remote Similarity	NPD7033	Discontinued
0.6748	Remote Similarity	NPD7003	Approved
0.6747	Remote Similarity	NPD6273	Approved
0.6742	Remote Similarity	NPD7472	Approved
0.6733	Remote Similarity	NPD5846	Approved
0.6733	Remote Similarity	NPD6516	Phase 2
0.6731	Remote Similarity	NPD7095	Approved
0.6727	Remote Similarity	NPD1511	Approved
0.6724	Remote Similarity	NPD8127	Discontinued
0.6722	Remote Similarity	NPD7549	Discontinued
0.6722	Remote Similarity	NPD7808	Phase 3
0.6721	Remote Similarity	NPD7906	Approved
0.6712	Remote Similarity	NPD5283	Phase 1
0.6711	Remote Similarity	NPD1840	Phase 2
0.6711	Remote Similarity	NPD2981	Phase 2
0.6711	Remote Similarity	NPD7741	Discontinued
0.6711	Remote Similarity	NPD3091	Approved
0.671	Remote Similarity	NPD1712	Approved
0.6691	Remote Similarity	NPD1242	Phase 1
0.669	Remote Similarity	NPD968	Approved
0.6688	Remote Similarity	NPD3094	Phase 2
0.6688	Remote Similarity	NPD2797	Approved
0.6688	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD7020	Approved
0.6687	Remote Similarity	NPD2532	Approved
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2534	Approved
0.6687	Remote Similarity	NPD2533	Approved
0.6687	Remote Similarity	NPD7019	Approved
0.6685	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3444	Approved
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3443	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD3445	Approved
0.6667	Remote Similarity	NPD1465	Phase 2
0.6648	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7833	Phase 2
0.6647	Remote Similarity	NPD1512	Approved
0.6647	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7831	Phase 2
0.6647	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8032	Phase 2
0.6645	Remote Similarity	NPD3705	Approved
0.6645	Remote Similarity	NPD3092	Approved
0.6644	Remote Similarity	NPD5535	Approved
0.6643	Remote Similarity	NPD940	Approved
0.6643	Remote Similarity	NPD846	Approved
0.6629	Remote Similarity	NPD3751	Discontinued
0.6629	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2563	Approved
0.6628	Remote Similarity	NPD2560	Approved
0.6628	Remote Similarity	NPD5402	Approved
0.6627	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3225	Approved
0.6623	Remote Similarity	NPD4626	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