NPASS Compound

Structure

NPC194323 OpenBabel07101718312D 35 38 0 0 1 0 0 0 0 0999 V2000 4.3950 -3.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6613 1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2848 1.1372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2256 -0.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0766 -1.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5289 -2.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7997 -0.2094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6629 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8950 -2.5007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2715 0.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3950 -1.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4940 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5289 -0.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2658 -1.8565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5289 -1.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7969 1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8950 -2.5007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8950 -0.7686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8950 -0.7686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6629 0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3950 1.4220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2686 -1.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 0.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2959 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2948 -0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3950 -1.6347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7969 -0.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6629 1.3653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3950 2.4220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2314 -2.6478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1629 2.2314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5185 0.0132 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 19 1 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 0 0 0 0 21 11 1 1 0 0 0 21 34 1 0 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 25 29 1 1 0 0 0 25 35 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 30 8 1 1 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	531.888
LogP:	5.267
LogD:	3.531
LogS:	-0.318
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	5.351
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.614
MDCK Permeability:	1.4035557796887588e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.92
30% Bioavailability (F30%):	0.767

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.706
Plasma Protein Binding (PPB):	72.2861099243164%
Volume Distribution (VD):	1.297
Pgp-substrate:	15.597761154174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.572

ADMET: Excretion

Clearance (CL):	14.476
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.128
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.575
Carcinogencity:	0.955
Eye Corrosion:	0.071
Eye Irritation:	0.016
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC194323

Natural Product ID:	NPC194323
*Common Name:**	Sodwanone S
IUPAC Name:	(5aS,6S,7S,9aS)-6-[2-[(3S,6S,7S,9aS)-3-hydroxy-2,2,6,7-tetramethyl-3,4,7,8,9,9a-hexahydro-1-benzoxepin-6-yl]ethyl]-7-hydroxy-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydrobenzo[b]oxepin-3-one
Synonyms:	Sodwanone S
Standard InCHIKey:	KKTMKQNIICOHDR-UDZSLJHISA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-19-9-11-21-20(10-12-23(31)26(2,3)34-21)28(19,6)16-13-22-29(7)17-14-24(32)27(4,5)35-25(29)15-18-30(22,8)33/h10,19,21-23,25,31,33H,9,11-18H2,1-8H3/t19-,21-,22-,23-,25-,28-,29-,30-/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=CC[C@@H](C(C)(C)O2)O)[C@@]1(C)CC[C@H]1[C@]2(C)CCC(=O)C(C)(C)O[C@H]2CC[C@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469635
PubChem CID:	11540437
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16124780]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9249974]
NPO28587	Axinella weltneri	Species	n.a.	n.a.	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	13

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[568518]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[568518]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	3.8	ug.mL-1	PMID[568518]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	6.5	ug.mL-1	PMID[568518]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[568518]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	4.1	ug.mL-1	PMID[568518]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[568518]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	6.9	ug.mL-1	PMID[568518]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[568518]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[568518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[568518]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.7	ug.mL-1	PMID[568518]

☑ 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 NPC194323 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	232
0.1-0.2	1420
0.2-0.3	4441
0.3-0.4	8383
0.4-0.5	14377
0.5-0.6	7730
0.6-0.7	5490
0.7-0.8	610
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8878	High Similarity	NPC474977
0.8571	High Similarity	NPC293086
0.835	Intermediate Similarity	NPC470840
0.8317	Intermediate Similarity	NPC285513
0.8317	Intermediate Similarity	NPC254496
0.8218	Intermediate Similarity	NPC260223
0.82	Intermediate Similarity	NPC212812
0.8137	Intermediate Similarity	NPC470834
0.8137	Intermediate Similarity	NPC272451
0.8119	Intermediate Similarity	NPC134067
0.8113	Intermediate Similarity	NPC475414
0.8113	Intermediate Similarity	NPC173172
0.8037	Intermediate Similarity	NPC473169
0.8037	Intermediate Similarity	NPC475176
0.8037	Intermediate Similarity	NPC144459
0.802	Intermediate Similarity	NPC472976
0.802	Intermediate Similarity	NPC472977
0.8019	Intermediate Similarity	NPC40170
0.8	Intermediate Similarity	NPC248913
0.8	Intermediate Similarity	NPC472975
0.7925	Intermediate Similarity	NPC90177
0.789	Intermediate Similarity	NPC87335
0.7876	Intermediate Similarity	NPC473590
0.785	Intermediate Similarity	NPC118911
0.783	Intermediate Similarity	NPC474709
0.7822	Intermediate Similarity	NPC111883
0.7818	Intermediate Similarity	NPC475563
0.7818	Intermediate Similarity	NPC475134
0.781	Intermediate Similarity	NPC473176
0.7778	Intermediate Similarity	NPC472645
0.7768	Intermediate Similarity	NPC311592
0.7768	Intermediate Similarity	NPC75167
0.7767	Intermediate Similarity	NPC316215
0.7757	Intermediate Similarity	NPC470839
0.7748	Intermediate Similarity	NPC475668
0.7748	Intermediate Similarity	NPC475480
0.7748	Intermediate Similarity	NPC473921
0.7736	Intermediate Similarity	NPC472643
0.7736	Intermediate Similarity	NPC476897
0.7736	Intermediate Similarity	NPC303559
0.7727	Intermediate Similarity	NPC141350
0.7714	Intermediate Similarity	NPC17183
0.7714	Intermediate Similarity	NPC303777
0.7714	Intermediate Similarity	NPC471784
0.7706	Intermediate Similarity	NPC131665
0.7706	Intermediate Similarity	NPC67321
0.7706	Intermediate Similarity	NPC187435
0.7706	Intermediate Similarity	NPC255387
0.7699	Intermediate Similarity	NPC181145
0.7692	Intermediate Similarity	NPC91439
0.7685	Intermediate Similarity	NPC75531
0.7685	Intermediate Similarity	NPC149124
0.7685	Intermediate Similarity	NPC258532
0.7679	Intermediate Similarity	NPC474516
0.7677	Intermediate Similarity	NPC202394
0.7672	Intermediate Similarity	NPC109607
0.7672	Intermediate Similarity	NPC107338
0.767	Intermediate Similarity	NPC470957
0.767	Intermediate Similarity	NPC470958
0.767	Intermediate Similarity	NPC196227
0.7664	Intermediate Similarity	NPC162973
0.7664	Intermediate Similarity	NPC185530
0.7647	Intermediate Similarity	NPC475972
0.7647	Intermediate Similarity	NPC472978
0.7642	Intermediate Similarity	NPC472644
0.7642	Intermediate Similarity	NPC474718
0.7642	Intermediate Similarity	NPC46761
0.7632	Intermediate Similarity	NPC470628
0.7632	Intermediate Similarity	NPC179626
0.7632	Intermediate Similarity	NPC474046
0.7632	Intermediate Similarity	NPC474734
0.7632	Intermediate Similarity	NPC259306
0.7629	Intermediate Similarity	NPC48362
0.7624	Intermediate Similarity	NPC97103
0.7624	Intermediate Similarity	NPC472973
0.7624	Intermediate Similarity	NPC115607
0.7619	Intermediate Similarity	NPC474343
0.7615	Intermediate Similarity	NPC478052
0.7615	Intermediate Similarity	NPC32006
0.7615	Intermediate Similarity	NPC85529
0.7615	Intermediate Similarity	NPC127609
0.7611	Intermediate Similarity	NPC477266
0.7596	Intermediate Similarity	NPC473170
0.7596	Intermediate Similarity	NPC477437
0.7596	Intermediate Similarity	NPC53565
0.7596	Intermediate Similarity	NPC272617
0.7596	Intermediate Similarity	NPC477438
0.7593	Intermediate Similarity	NPC26478
0.7589	Intermediate Similarity	NPC317107
0.7586	Intermediate Similarity	NPC473636
0.7586	Intermediate Similarity	NPC211093
0.7586	Intermediate Similarity	NPC77689
0.7586	Intermediate Similarity	NPC473839
0.7586	Intermediate Similarity	NPC475775
0.7586	Intermediate Similarity	NPC476529
0.7576	Intermediate Similarity	NPC79573
0.7576	Intermediate Similarity	NPC290731
0.7573	Intermediate Similarity	NPC53555
0.7573	Intermediate Similarity	NPC477436
0.7573	Intermediate Similarity	NPC477435
0.757	Intermediate Similarity	NPC472637
0.757	Intermediate Similarity	NPC471412
0.757	Intermediate Similarity	NPC323441
0.7568	Intermediate Similarity	NPC472216
0.7568	Intermediate Similarity	NPC42662
0.7568	Intermediate Similarity	NPC284828
0.7568	Intermediate Similarity	NPC5475
0.7568	Intermediate Similarity	NPC475065
0.7568	Intermediate Similarity	NPC173905
0.7565	Intermediate Similarity	NPC476713
0.7565	Intermediate Similarity	NPC476712
0.7565	Intermediate Similarity	NPC134430
0.7565	Intermediate Similarity	NPC475809
0.7563	Intermediate Similarity	NPC470922
0.7551	Intermediate Similarity	NPC222358
0.7549	Intermediate Similarity	NPC472325
0.7549	Intermediate Similarity	NPC128672
0.7549	Intermediate Similarity	NPC134321
0.7547	Intermediate Similarity	NPC316598
0.7545	Intermediate Similarity	NPC329048
0.7545	Intermediate Similarity	NPC230541
0.7545	Intermediate Similarity	NPC330011
0.7545	Intermediate Similarity	NPC3316
0.7545	Intermediate Similarity	NPC469318
0.7545	Intermediate Similarity	NPC473173
0.7545	Intermediate Similarity	NPC475294
0.7545	Intermediate Similarity	NPC144854
0.7544	Intermediate Similarity	NPC469877
0.7544	Intermediate Similarity	NPC80650
0.7544	Intermediate Similarity	NPC470919
0.7525	Intermediate Similarity	NPC475001
0.7525	Intermediate Similarity	NPC185059
0.7524	Intermediate Similarity	NPC94337
0.7524	Intermediate Similarity	NPC160056
0.7523	Intermediate Similarity	NPC284865
0.7522	Intermediate Similarity	NPC277769
0.7522	Intermediate Similarity	NPC174836
0.7522	Intermediate Similarity	NPC4573
0.7522	Intermediate Similarity	NPC473877
0.7522	Intermediate Similarity	NPC90769
0.7522	Intermediate Similarity	NPC317687
0.75	Intermediate Similarity	NPC477439
0.75	Intermediate Similarity	NPC5103
0.75	Intermediate Similarity	NPC83005
0.75	Intermediate Similarity	NPC136289
0.75	Intermediate Similarity	NPC476081
0.75	Intermediate Similarity	NPC251310
0.75	Intermediate Similarity	NPC476217
0.75	Intermediate Similarity	NPC311554
0.75	Intermediate Similarity	NPC80781
0.75	Intermediate Similarity	NPC103527
0.75	Intermediate Similarity	NPC257457
0.7479	Intermediate Similarity	NPC265557
0.7479	Intermediate Similarity	NPC91693
0.7479	Intermediate Similarity	NPC18945
0.7479	Intermediate Similarity	NPC105926
0.7479	Intermediate Similarity	NPC67251
0.7478	Intermediate Similarity	NPC476711
0.7478	Intermediate Similarity	NPC476710
0.7478	Intermediate Similarity	NPC474333
0.7478	Intermediate Similarity	NPC471816
0.7478	Intermediate Similarity	NPC328374
0.7478	Intermediate Similarity	NPC251236
0.7478	Intermediate Similarity	NPC40632
0.7478	Intermediate Similarity	NPC134869
0.7478	Intermediate Similarity	NPC478216
0.7478	Intermediate Similarity	NPC152199
0.7478	Intermediate Similarity	NPC235539
0.7478	Intermediate Similarity	NPC96312
0.7477	Intermediate Similarity	NPC476479
0.7477	Intermediate Similarity	NPC217201
0.7477	Intermediate Similarity	NPC473482
0.7477	Intermediate Similarity	NPC208461
0.7477	Intermediate Similarity	NPC471413
0.7477	Intermediate Similarity	NPC117685
0.7477	Intermediate Similarity	NPC154608
0.7477	Intermediate Similarity	NPC192813
0.7477	Intermediate Similarity	NPC289702
0.7477	Intermediate Similarity	NPC475418
0.7477	Intermediate Similarity	NPC306265
0.7477	Intermediate Similarity	NPC472972
0.7477	Intermediate Similarity	NPC277017
0.7477	Intermediate Similarity	NPC318363
0.7477	Intermediate Similarity	NPC293850
0.7476	Intermediate Similarity	NPC475441
0.7476	Intermediate Similarity	NPC473166
0.7476	Intermediate Similarity	NPC116726
0.7475	Intermediate Similarity	NPC40687
0.7459	Intermediate Similarity	NPC476854
0.7458	Intermediate Similarity	NPC470779
0.7456	Intermediate Similarity	NPC108721
0.7456	Intermediate Similarity	NPC7921
0.7456	Intermediate Similarity	NPC469454
0.7456	Intermediate Similarity	NPC208998
0.7456	Intermediate Similarity	NPC469496
0.7456	Intermediate Similarity	NPC469463
0.7456	Intermediate Similarity	NPC471204
0.7456	Intermediate Similarity	NPC73300
0.7455	Intermediate Similarity	NPC60681
0.7455	Intermediate Similarity	NPC477125

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 NPC194323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1716
0.2-0.3	3762
0.3-0.4	2250
0.4-0.5	775
0.5-0.6	263
0.6-0.7	158
0.7-0.8	15
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
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6675	Approved
0.7455	Intermediate Similarity	NPD6402	Approved
0.7455	Intermediate Similarity	NPD7128	Approved
0.7455	Intermediate Similarity	NPD5739	Approved
0.7368	Intermediate Similarity	NPD8297	Approved
0.7321	Intermediate Similarity	NPD6881	Approved
0.7321	Intermediate Similarity	NPD7320	Approved
0.7321	Intermediate Similarity	NPD6899	Approved
0.729	Intermediate Similarity	NPD4755	Approved
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD5697	Approved
0.7232	Intermediate Similarity	NPD5701	Approved
0.7222	Intermediate Similarity	NPD4225	Approved
0.7193	Intermediate Similarity	NPD7290	Approved
0.7193	Intermediate Similarity	NPD7102	Approved
0.7193	Intermediate Similarity	NPD6883	Approved
0.7182	Intermediate Similarity	NPD5211	Phase 2
0.7168	Intermediate Similarity	NPD6011	Approved
0.7156	Intermediate Similarity	NPD4700	Approved
0.7156	Intermediate Similarity	NPD5286	Approved
0.7156	Intermediate Similarity	NPD5285	Approved
0.7156	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.7119	Intermediate Similarity	NPD7115	Discovery
0.7115	Intermediate Similarity	NPD5328	Approved
0.7105	Intermediate Similarity	NPD6013	Approved
0.7105	Intermediate Similarity	NPD6014	Approved
0.7105	Intermediate Similarity	NPD6012	Approved
0.7091	Intermediate Similarity	NPD5223	Approved
0.7069	Intermediate Similarity	NPD6882	Approved
0.7054	Intermediate Similarity	NPD5141	Approved
0.7037	Intermediate Similarity	NPD4697	Phase 3
0.7037	Intermediate Similarity	NPD5221	Approved
0.7037	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5222	Approved
0.7027	Intermediate Similarity	NPD4633	Approved
0.7027	Intermediate Similarity	NPD5224	Approved
0.7027	Intermediate Similarity	NPD5226	Approved
0.7027	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.6981	Remote Similarity	NPD6079	Approved
0.6972	Remote Similarity	NPD5173	Approved
0.6964	Remote Similarity	NPD5175	Approved
0.6964	Remote Similarity	NPD4754	Approved
0.6964	Remote Similarity	NPD5174	Approved
0.6961	Remote Similarity	NPD4786	Approved
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6319	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD6054	Approved
0.6931	Remote Similarity	NPD3667	Approved
0.6916	Remote Similarity	NPD6399	Phase 3
0.6909	Remote Similarity	NPD7638	Approved
0.6897	Remote Similarity	NPD4634	Approved
0.687	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD7748	Approved
0.6847	Remote Similarity	NPD7640	Approved
0.6847	Remote Similarity	NPD7639	Approved
0.6842	Remote Similarity	NPD4768	Approved
0.6842	Remote Similarity	NPD4767	Approved
0.6833	Remote Similarity	NPD6009	Approved
0.6829	Remote Similarity	NPD6370	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD7515	Phase 2
0.6818	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD7902	Approved
0.6818	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD7507	Approved
0.6777	Remote Similarity	NPD6335	Approved
0.6774	Remote Similarity	NPD7604	Phase 2
0.6774	Remote Similarity	NPD8328	Phase 3
0.6759	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD6274	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6748	Remote Similarity	NPD5983	Phase 2
0.6748	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6733	Remote Similarity	NPD4695	Discontinued
0.6724	Remote Similarity	NPD4729	Approved
0.6724	Remote Similarity	NPD4730	Approved
0.6724	Remote Similarity	NPD5128	Approved
0.6721	Remote Similarity	NPD7101	Approved
0.6721	Remote Similarity	NPD7100	Approved
0.672	Remote Similarity	NPD7492	Approved
0.6694	Remote Similarity	NPD6317	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6641	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD6313	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD4753	Phase 2
0.6614	Remote Similarity	NPD7078	Approved
0.6614	Remote Similarity	NPD8293	Discontinued
0.6613	Remote Similarity	NPD6909	Approved
0.6613	Remote Similarity	NPD6908	Approved
0.6612	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD5249	Phase 3
0.661	Remote Similarity	NPD5248	Approved
0.661	Remote Similarity	NPD5135	Approved
0.661	Remote Similarity	NPD5247	Approved
0.661	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5250	Approved
0.661	Remote Similarity	NPD5251	Approved
0.661	Remote Similarity	NPD6371	Approved
0.661	Remote Similarity	NPD5169	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD46	Approved
0.6574	Remote Similarity	NPD6698	Approved
0.6569	Remote Similarity	NPD7525	Registered
0.6562	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD6033	Approved
0.6555	Remote Similarity	NPD5216	Approved
0.6555	Remote Similarity	NPD5127	Approved
0.6555	Remote Similarity	NPD5215	Approved
0.6555	Remote Similarity	NPD5217	Approved
0.6545	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7900	Approved
0.6542	Remote Similarity	NPD5737	Approved
0.6542	Remote Similarity	NPD6672	Approved
0.6514	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD6053	Discontinued
0.6496	Remote Similarity	NPD6412	Phase 2
0.6486	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5695	Phase 3
0.6481	Remote Similarity	NPD6101	Approved
0.6481	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3668	Phase 3
0.6476	Remote Similarity	NPD3665	Phase 1
0.6476	Remote Similarity	NPD3666	Approved
0.646	Remote Similarity	NPD5696	Approved
0.6449	Remote Similarity	NPD7524	Approved
0.6449	Remote Similarity	NPD3573	Approved
0.6441	Remote Similarity	NPD5168	Approved
0.6415	Remote Similarity	NPD5329	Approved
0.641	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5167	Approved
0.6387	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7328	Approved
0.6371	Remote Similarity	NPD7327	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD7983	Approved
0.6364	Remote Similarity	NPD8035	Phase 2
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6098	Approved
0.6349	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4629	Approved
0.6339	Remote Similarity	NPD5210	Approved
0.6337	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD6904	Approved
0.633	Remote Similarity	NPD6673	Approved
0.633	Remote Similarity	NPD6080	Approved
0.6321	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4197	Approved
0.632	Remote Similarity	NPD7516	Approved
0.6311	Remote Similarity	NPD8133	Approved
0.6311	Remote Similarity	NPD7645	Phase 2
0.6293	Remote Similarity	NPD7632	Discontinued
0.6281	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD1696	Phase 3
0.6262	Remote Similarity	NPD1694	Approved
0.6262	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6226	Remote Similarity	NPD6695	Phase 3
0.6226	Remote Similarity	NPD6110	Phase 1
0.622	Remote Similarity	NPD8033	Approved
0.622	Remote Similarity	NPD8516	Approved
0.622	Remote Similarity	NPD8515	Approved
0.622	Remote Similarity	NPD8513	Phase 3
0.622	Remote Similarity	NPD8517	Approved
0.6204	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5330	Approved
0.6204	Remote Similarity	NPD6409	Approved
0.6204	Remote Similarity	NPD7146	Approved
0.6204	Remote Similarity	NPD6684	Approved
0.6204	Remote Similarity	NPD7521	Approved
0.6204	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD7334	Approved
0.6204	Remote Similarity	NPD4623	Approved
0.6182	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD7260	Phase 2

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