NPASS Compound

Structure

NPC17183 OpenBabel07101719152D 38 41 0 0 1 0 0 0 0 0999 V2000 -0.1895 2.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 0.4336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7395 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8886 0.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5027 3.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9089 4.2646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2075 3.1018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8632 0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0353 3.8637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0012 4.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 2.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0426 1.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0433 1.6449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7170 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7765 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9196 1.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4836 2.1907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3944 2.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6949 2.3655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7083 3.4154 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9577 1.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5090 3.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 2.4495 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8856 0.8819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8944 3.0132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7934 -0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6608 2.1067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6249 3.8153 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6629 0.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 9 31 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 21 32 1 1 0 0 0 22 33 2 0 0 0 0 22 36 1 0 0 0 0 23 30 1 6 0 0 0 24 28 1 0 0 0 0 24 34 2 0 0 0 0 25 29 1 0 0 0 0 25 36 1 6 0 0 0 26 30 1 6 0 0 0 26 37 1 0 0 0 0 27 31 1 6 0 0 0 27 38 1 0 0 0 0 28 38 1 0 0 0 0 29 37 1 0 0 0 0 30 8 1 6 0 0 0 31 32 1 6 0 0 0 32 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.38
Volume:	572.634
LogP:	4.852
LogD:	3.588
LogS:	-4.23
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	5.292
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.672
MDCK Permeability:	1.7130645574070513e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.77
30% Bioavailability (F30%):	0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.567
Plasma Protein Binding (PPB):	79.1363754272461%
Volume Distribution (VD):	1.37
Pgp-substrate:	12.046670913696289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.087
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.537
CYP3A4-inhibitor:	0.563
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	5.369
Half-life (T1/2):	0.345

ADMET: Toxicity

hERG Blockers:	0.327
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.398
Maximum Recommended Daily Dose:	0.872
Skin Sensitization:	0.459
Carcinogencity:	0.515
Eye Corrosion:	0.014
Eye Irritation:	0.014
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC17183

Natural Product ID:	NPC17183
*Common Name:**	3-Epi-Sodwanone K 3-Acetate
IUPAC Name:	[(3R,5aS,6R,9aS)-6-[2-[(5aR,6S,7S,9aS)-6-hydroxy-2,2,5a,7-tetramethyl-3-oxo-4,5,7,8,9,9a-hexahydrobenzo[b]oxepin-6-yl]ethyl]-2,2,5a-trimethyl-7-methylidene-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepin-3-yl] acetate
Synonyms:
Standard InCHIKey:	WZPVVCITGYFTEY-SYGGFZANSA-N
Standard InCHI:	InChI=1S/C32H52O6/c1-20-10-12-26-30(8,17-16-25(36-22(3)33)29(6,7)37-26)23(20)14-19-32(35)21(2)11-13-27-31(32,9)18-15-24(34)28(4,5)38-27/h21,23,25-27,35H,1,10-19H2,2-9H3/t21-,23+,25+,26-,27-,30-,31+,32-/m0/s1
SMILES:	CC(=O)O[C@@H]1CC[C@@]2([C@@H](OC1(C)C)CCC(=C)[C@H]2CC[C@]1(O)[C@@H](C)CC[C@H]2[C@@]1(C)CCC(=O)C(O2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494658
PubChem CID:	16099424
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32663	Axinella	Genus	Axinellidae	Eukaryota	n.a.	South African	n.a.	PMID[17190448]

☑ 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	7

Activity Type	# Activity
Cell Line	4
PROTEIN FAMILY	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	22000.0	nM	PMID[494683]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	30000.0	nM	PMID[494683]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	30000.0	nM	PMID[494683]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	30000.0	nM	PMID[494683]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	20000.0	nM	PMID[494683]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[494683]

☑ 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 NPC17183 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	264
0.1-0.2	2089
0.2-0.3	6135
0.3-0.4	12457
0.4-0.5	10082
0.5-0.6	7059
0.6-0.7	4340
0.7-0.8	269
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC260223
0.8544	High Similarity	NPC16657
0.8544	High Similarity	NPC204652
0.8447	Intermediate Similarity	NPC153587
0.8119	Intermediate Similarity	NPC293890
0.8113	Intermediate Similarity	NPC100908
0.8037	Intermediate Similarity	NPC157476
0.8	Intermediate Similarity	NPC219353
0.7963	Intermediate Similarity	NPC474516
0.7959	Intermediate Similarity	NPC198054
0.7905	Intermediate Similarity	NPC50535
0.7843	Intermediate Similarity	NPC162459
0.7843	Intermediate Similarity	NPC28864
0.7843	Intermediate Similarity	NPC38471
0.7843	Intermediate Similarity	NPC477653
0.7843	Intermediate Similarity	NPC98837
0.7843	Intermediate Similarity	NPC38296
0.7843	Intermediate Similarity	NPC20479
0.7843	Intermediate Similarity	NPC472028
0.783	Intermediate Similarity	NPC251824
0.783	Intermediate Similarity	NPC176949
0.783	Intermediate Similarity	NPC86852
0.783	Intermediate Similarity	NPC201908
0.7818	Intermediate Similarity	NPC473798
0.781	Intermediate Similarity	NPC301787
0.781	Intermediate Similarity	NPC47281
0.78	Intermediate Similarity	NPC272635
0.78	Intermediate Similarity	NPC169751
0.78	Intermediate Similarity	NPC293086
0.7778	Intermediate Similarity	NPC111883
0.7767	Intermediate Similarity	NPC293866
0.7767	Intermediate Similarity	NPC94906
0.7767	Intermediate Similarity	NPC472972
0.7757	Intermediate Similarity	NPC208461
0.7757	Intermediate Similarity	NPC289702
0.7748	Intermediate Similarity	NPC328374
0.7748	Intermediate Similarity	NPC40632
0.7748	Intermediate Similarity	NPC96312
0.7748	Intermediate Similarity	NPC251236
0.7745	Intermediate Similarity	NPC111348
0.7736	Intermediate Similarity	NPC138908
0.7736	Intermediate Similarity	NPC28791
0.7736	Intermediate Similarity	NPC200957
0.7736	Intermediate Similarity	NPC222833
0.7723	Intermediate Similarity	NPC470229
0.7723	Intermediate Similarity	NPC322188
0.7714	Intermediate Similarity	NPC225238
0.7714	Intermediate Similarity	NPC469985
0.7714	Intermediate Similarity	NPC194323
0.7692	Intermediate Similarity	NPC121218
0.7692	Intermediate Similarity	NPC253886
0.7692	Intermediate Similarity	NPC46848
0.7692	Intermediate Similarity	NPC252614
0.7685	Intermediate Similarity	NPC310546
0.767	Intermediate Similarity	NPC474793
0.767	Intermediate Similarity	NPC474724
0.767	Intermediate Similarity	NPC89099
0.767	Intermediate Similarity	NPC119036
0.7664	Intermediate Similarity	NPC166993
0.7647	Intermediate Similarity	NPC329910
0.7647	Intermediate Similarity	NPC256227
0.7647	Intermediate Similarity	NPC200054
0.7647	Intermediate Similarity	NPC29410
0.7642	Intermediate Similarity	NPC65523
0.7636	Intermediate Similarity	NPC280782
0.7636	Intermediate Similarity	NPC152117
0.7636	Intermediate Similarity	NPC234042
0.7624	Intermediate Similarity	NPC477439
0.7624	Intermediate Similarity	NPC76136
0.7624	Intermediate Similarity	NPC217567
0.7624	Intermediate Similarity	NPC329713
0.7624	Intermediate Similarity	NPC469982
0.7624	Intermediate Similarity	NPC475118
0.7624	Intermediate Similarity	NPC476722
0.7619	Intermediate Similarity	NPC214946
0.7619	Intermediate Similarity	NPC246736
0.7619	Intermediate Similarity	NPC304832
0.7619	Intermediate Similarity	NPC88203
0.7619	Intermediate Similarity	NPC124544
0.7619	Intermediate Similarity	NPC76866
0.7619	Intermediate Similarity	NPC286519
0.7619	Intermediate Similarity	NPC170615
0.7619	Intermediate Similarity	NPC148628
0.7619	Intermediate Similarity	NPC275990
0.7609	Intermediate Similarity	NPC474433
0.76	Intermediate Similarity	NPC476934
0.76	Intermediate Similarity	NPC248913
0.7596	Intermediate Similarity	NPC477656
0.7593	Intermediate Similarity	NPC255082
0.7593	Intermediate Similarity	NPC293850
0.7593	Intermediate Similarity	NPC273155
0.7589	Intermediate Similarity	NPC235539
0.7589	Intermediate Similarity	NPC474734
0.7589	Intermediate Similarity	NPC134869
0.7589	Intermediate Similarity	NPC152199
0.7576	Intermediate Similarity	NPC77001
0.7576	Intermediate Similarity	NPC269267
0.7576	Intermediate Similarity	NPC253618
0.7573	Intermediate Similarity	NPC272451
0.7573	Intermediate Similarity	NPC190080
0.7573	Intermediate Similarity	NPC10864
0.7573	Intermediate Similarity	NPC476878
0.7573	Intermediate Similarity	NPC111187
0.7573	Intermediate Similarity	NPC476879
0.757	Intermediate Similarity	NPC196528
0.757	Intermediate Similarity	NPC477877
0.7568	Intermediate Similarity	NPC208998
0.7568	Intermediate Similarity	NPC7921
0.7568	Intermediate Similarity	NPC49451
0.7549	Intermediate Similarity	NPC98639
0.7549	Intermediate Similarity	NPC477438
0.7549	Intermediate Similarity	NPC470232
0.7549	Intermediate Similarity	NPC266899
0.7549	Intermediate Similarity	NPC477437
0.7547	Intermediate Similarity	NPC277074
0.7547	Intermediate Similarity	NPC209298
0.7547	Intermediate Similarity	NPC122811
0.7545	Intermediate Similarity	NPC146945
0.7545	Intermediate Similarity	NPC171888
0.7526	Intermediate Similarity	NPC477445
0.7525	Intermediate Similarity	NPC477436
0.7525	Intermediate Similarity	NPC147272
0.7525	Intermediate Similarity	NPC294263
0.7525	Intermediate Similarity	NPC477435
0.7524	Intermediate Similarity	NPC295276
0.7524	Intermediate Similarity	NPC477052
0.7524	Intermediate Similarity	NPC289148
0.7524	Intermediate Similarity	NPC163963
0.7524	Intermediate Similarity	NPC477053
0.7524	Intermediate Similarity	NPC52899
0.7524	Intermediate Similarity	NPC75941
0.7524	Intermediate Similarity	NPC236585
0.7524	Intermediate Similarity	NPC477051
0.7523	Intermediate Similarity	NPC154906
0.7522	Intermediate Similarity	NPC473590
0.75	Intermediate Similarity	NPC18547
0.75	Intermediate Similarity	NPC474906
0.75	Intermediate Similarity	NPC477444
0.75	Intermediate Similarity	NPC469318
0.75	Intermediate Similarity	NPC232202
0.75	Intermediate Similarity	NPC477433
0.75	Intermediate Similarity	NPC46758
0.75	Intermediate Similarity	NPC473173
0.75	Intermediate Similarity	NPC471038
0.75	Intermediate Similarity	NPC3316
0.75	Intermediate Similarity	NPC477442
0.75	Intermediate Similarity	NPC144854
0.7477	Intermediate Similarity	NPC471293
0.7477	Intermediate Similarity	NPC90769
0.7476	Intermediate Similarity	NPC471822
0.7476	Intermediate Similarity	NPC473964
0.7475	Intermediate Similarity	NPC163296
0.7475	Intermediate Similarity	NPC50847
0.7475	Intermediate Similarity	NPC229407
0.7475	Intermediate Similarity	NPC48824
0.7475	Intermediate Similarity	NPC254572
0.7475	Intermediate Similarity	NPC476435
0.7475	Intermediate Similarity	NPC250687
0.7456	Intermediate Similarity	NPC17772
0.7456	Intermediate Similarity	NPC297179
0.7453	Intermediate Similarity	NPC477054
0.7451	Intermediate Similarity	NPC47853
0.7451	Intermediate Similarity	NPC470385
0.7451	Intermediate Similarity	NPC470386
0.7451	Intermediate Similarity	NPC212812
0.7451	Intermediate Similarity	NPC476716
0.7434	Intermediate Similarity	NPC474046
0.7434	Intermediate Similarity	NPC207217
0.7434	Intermediate Similarity	NPC16081
0.7434	Intermediate Similarity	NPC470628
0.7434	Intermediate Similarity	NPC173686
0.7434	Intermediate Similarity	NPC259306
0.7434	Intermediate Similarity	NPC179626
0.7431	Intermediate Similarity	NPC218123
0.7431	Intermediate Similarity	NPC258323
0.7431	Intermediate Similarity	NPC154608
0.7431	Intermediate Similarity	NPC112895
0.7431	Intermediate Similarity	NPC192813
0.7431	Intermediate Similarity	NPC277017
0.7431	Intermediate Similarity	NPC94529
0.7431	Intermediate Similarity	NPC231278
0.7431	Intermediate Similarity	NPC94942
0.7429	Intermediate Similarity	NPC41971
0.7429	Intermediate Similarity	NPC37047
0.7429	Intermediate Similarity	NPC287676
0.7429	Intermediate Similarity	NPC180733
0.7429	Intermediate Similarity	NPC471413
0.7429	Intermediate Similarity	NPC477655
0.7429	Intermediate Similarity	NPC167974
0.7426	Intermediate Similarity	NPC329952
0.7426	Intermediate Similarity	NPC165180
0.7426	Intermediate Similarity	NPC470230
0.7426	Intermediate Similarity	NPC216137
0.7423	Intermediate Similarity	NPC477434
0.7423	Intermediate Similarity	NPC97505
0.7411	Intermediate Similarity	NPC198539
0.7407	Intermediate Similarity	NPC295366
0.7407	Intermediate Similarity	NPC37600
0.7404	Intermediate Similarity	NPC470834
0.7404	Intermediate Similarity	NPC253586

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 NPC17183 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	2558
0.2-0.3	3842
0.3-0.4	1624
0.4-0.5	477
0.5-0.6	257
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
0.7757	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD8297	Approved
0.7407	Intermediate Similarity	NPD5739	Approved
0.7407	Intermediate Similarity	NPD7128	Approved
0.7407	Intermediate Similarity	NPD6675	Approved
0.7407	Intermediate Similarity	NPD6402	Approved
0.7273	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6899	Approved
0.7273	Intermediate Similarity	NPD6881	Approved
0.7232	Intermediate Similarity	NPD8130	Phase 1
0.7207	Intermediate Similarity	NPD6372	Approved
0.7207	Intermediate Similarity	NPD6373	Approved
0.7182	Intermediate Similarity	NPD5697	Approved
0.7182	Intermediate Similarity	NPD5701	Approved
0.7179	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7748	Approved
0.7107	Intermediate Similarity	NPD8293	Discontinued
0.7105	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD8035	Phase 2
0.7087	Intermediate Similarity	NPD8034	Phase 2
0.7083	Intermediate Similarity	NPD7492	Approved
0.708	Intermediate Similarity	NPD6617	Approved
0.708	Intermediate Similarity	NPD6869	Approved
0.708	Intermediate Similarity	NPD6649	Approved
0.708	Intermediate Similarity	NPD6650	Approved
0.708	Intermediate Similarity	NPD6847	Approved
0.7069	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6009	Approved
0.7054	Intermediate Similarity	NPD6013	Approved
0.7054	Intermediate Similarity	NPD6014	Approved
0.7054	Intermediate Similarity	NPD6012	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7034	Intermediate Similarity	NPD6059	Approved
0.7034	Intermediate Similarity	NPD6054	Approved
0.7025	Intermediate Similarity	NPD6616	Approved
0.7018	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD7604	Phase 2
0.6975	Remote Similarity	NPD5983	Phase 2
0.6975	Remote Similarity	NPD6921	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6964	Remote Similarity	NPD6011	Approved
0.693	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6370	Approved
0.6916	Remote Similarity	NPD6083	Phase 2
0.6916	Remote Similarity	NPD7902	Approved
0.6916	Remote Similarity	NPD6084	Phase 2
0.6903	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD6016	Approved
0.6832	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8133	Approved
0.6777	Remote Similarity	NPD5988	Approved
0.6762	Remote Similarity	NPD7515	Phase 2
0.6759	Remote Similarity	NPD4755	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5695	Phase 3
0.6698	Remote Similarity	NPD6399	Phase 3
0.6697	Remote Similarity	NPD7638	Approved
0.6697	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6637	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6635	Remote Similarity	NPD5737	Approved
0.6635	Remote Similarity	NPD6672	Approved
0.6604	Remote Similarity	NPD6411	Approved
0.6583	Remote Similarity	NPD6335	Approved
0.6577	Remote Similarity	NPD1700	Approved
0.6571	Remote Similarity	NPD5328	Approved
0.6557	Remote Similarity	NPD6909	Approved
0.6557	Remote Similarity	NPD6908	Approved
0.6555	Remote Similarity	NPD6868	Approved
0.6552	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD5779	Approved
0.6542	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6522	Remote Similarity	NPD6686	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6518	Remote Similarity	NPD5224	Approved
0.6514	Remote Similarity	NPD5221	Approved
0.6514	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4697	Phase 3
0.6514	Remote Similarity	NPD5222	Approved
0.6508	Remote Similarity	NPD6033	Approved
0.65	Remote Similarity	NPD6317	Approved
0.648	Remote Similarity	NPD7507	Approved
0.6465	Remote Similarity	NPD6697	Approved
0.6465	Remote Similarity	NPD6114	Approved
0.6465	Remote Similarity	NPD6118	Approved
0.6465	Remote Similarity	NPD6115	Approved
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6457	Remote Similarity	NPD7319	Approved
0.6455	Remote Similarity	NPD5173	Approved
0.6449	Remote Similarity	NPD6079	Approved
0.6446	Remote Similarity	NPD6314	Approved
0.6446	Remote Similarity	NPD6313	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD5223	Approved
0.6415	Remote Similarity	NPD6673	Approved
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6904	Approved
0.6415	Remote Similarity	NPD6080	Approved
0.6415	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD5141	Approved
0.6396	Remote Similarity	NPD4225	Approved
0.6364	Remote Similarity	NPD7115	Discovery
0.6348	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD4767	Approved
0.6327	Remote Similarity	NPD3703	Phase 2
0.6316	Remote Similarity	NPD4754	Approved
0.6296	Remote Similarity	NPD7983	Approved
0.6286	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD5330	Approved
0.6286	Remote Similarity	NPD6684	Approved
0.6286	Remote Similarity	NPD3618	Phase 1
0.6286	Remote Similarity	NPD7146	Approved
0.6286	Remote Similarity	NPD7521	Approved
0.6263	Remote Similarity	NPD6117	Approved
0.6262	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD4786	Approved
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD4729	Approved
0.6239	Remote Similarity	NPD4730	Approved
0.6228	Remote Similarity	NPD7632	Discontinued
0.6214	Remote Similarity	NPD3667	Approved
0.62	Remote Similarity	NPD6116	Phase 1
0.6182	Remote Similarity	NPD5282	Discontinued
0.6176	Remote Similarity	NPD4695	Discontinued
0.6168	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6053	Discontinued
0.616	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4788	Approved
0.6147	Remote Similarity	NPD6050	Approved
0.6147	Remote Similarity	NPD5693	Phase 1
0.6147	Remote Similarity	NPD7637	Suspended
0.614	Remote Similarity	NPD5344	Discontinued
0.6134	Remote Similarity	NPD6371	Approved
0.6134	Remote Similarity	NPD5247	Approved
0.6134	Remote Similarity	NPD5249	Phase 3
0.6134	Remote Similarity	NPD5248	Approved
0.6134	Remote Similarity	NPD5250	Approved
0.6134	Remote Similarity	NPD5251	Approved
0.6126	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD1779	Approved
0.6117	Remote Similarity	NPD1780	Approved
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4202	Approved
0.6083	Remote Similarity	NPD5216	Approved
0.6083	Remote Similarity	NPD5217	Approved
0.6083	Remote Similarity	NPD5215	Approved
0.6075	Remote Similarity	NPD7524	Approved
0.6061	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6435	Approved
0.6055	Remote Similarity	NPD6698	Approved
0.6055	Remote Similarity	NPD46	Approved
0.6055	Remote Similarity	NPD5692	Phase 3
0.6053	Remote Similarity	NPD6648	Approved
0.6048	Remote Similarity	NPD7328	Approved
0.6048	Remote Similarity	NPD7327	Approved
0.6038	Remote Similarity	NPD5329	Approved
0.6032	Remote Similarity	NPD8378	Approved
0.6032	Remote Similarity	NPD8296	Approved
0.6032	Remote Similarity	NPD8380	Approved
0.6032	Remote Similarity	NPD8335	Approved
0.6032	Remote Similarity	NPD8379	Approved
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3669	Approved
0.6	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD5135	Approved
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD5169	Approved
0.5982	Remote Similarity	NPD5210	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