NPASS Compound

Structure

NPC101067 OpenBabel07101718202D 50 53 0 0 1 0 0 0 0 0999 V2000 2.4927 2.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1286 1.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5465 -1.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1190 1.3655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8025 1.8232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2702 -2.0848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7807 2.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9175 -1.6513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2062 -2.8961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5462 0.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3840 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4642 0.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9434 1.1144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.2369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4668 -0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4668 0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 0.2752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4972 -1.0053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2327 -1.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1285 1.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9434 -1.1144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0794 0.3102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0791 2.0273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0096 -0.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3737 0.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1541 1.1245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6838 -1.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6161 1.2397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3737 -0.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 -0.2752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4716 -0.6889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6774 1.3997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9483 -0.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2417 0.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1299 1.1144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -1.2369 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5603 -0.7712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1040 -0.3762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5603 0.7712 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1299 -1.1144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1615 -0.2341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9584 2.3105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6673 -1.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4162 1.3128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5435 1.9732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.1901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6984 0.3691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0587 -2.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -2.1508 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 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 9 49 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 2 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 35 1 0 0 0 0 15 16 1 0 0 0 0 15 37 1 0 0 0 0 16 39 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 24 2 0 0 0 0 18 33 1 0 0 0 0 19 27 1 0 0 0 0 19 31 1 0 0 0 0 20 28 1 0 0 0 0 20 32 1 0 0 0 0 21 29 1 0 0 0 0 21 36 1 0 0 0 0 22 34 1 0 0 0 0 22 41 1 0 0 0 0 26 32 1 0 0 0 0 27 29 2 0 0 0 0 28 23 1 6 0 0 0 28 34 1 0 0 0 0 29 30 1 0 0 0 0 30 41 1 6 0 0 0 31 33 1 0 0 0 0 31 41 1 1 0 0 0 32 42 2 0 0 0 0 33 43 2 0 0 0 0 34 44 2 0 0 0 0 35 39 1 1 0 0 0 35 45 1 0 0 0 0 36 40 1 6 0 0 0 36 46 1 0 0 0 0 37 40 1 1 0 0 0 37 50 1 0 0 0 0 38 47 2 0 0 0 0 38 49 1 0 0 0 0 39 7 1 6 0 0 0 39 50 1 0 0 0 0 40 8 1 1 0 0 0 40 48 1 0 0 0 0 41 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.42
Volume:	741.486
LogP:	4.467
LogD:	3.044
LogS:	-4.447
# Rotatable Bonds:	2
TPSA:	147.43
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	6.996
Fsp3:	0.707
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:	-4.871
MDCK Permeability:	1.4871268831484485e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.946
20% Bioavailability (F20%):	0.157
30% Bioavailability (F30%):	0.45

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	87.77445220947266%
Volume Distribution (VD):	1.498
Pgp-substrate:	5.450246334075928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.743
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.849
CYP3A4-substrate:	0.518

ADMET: Excretion

Clearance (CL):	14.531
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.617
Carcinogencity:	0.913
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC101067

Natural Product ID:	NPC101067
*Common Name:**	Bisglaucumlide G
IUPAC Name:	n.a.
Synonyms:	Bisglaucumlide G
Standard InCHIKey:	APYCNDHUMQUETQ-DXFSNFGHSA-N
Standard InCHI:	InChI=1S/C41H60O9/c1-23(2)28-20-32(42)26(5)12-10-11-24(3)18-33(43)31-19-27(6)29-21-36(46)40(8,48)37-15-16-39(7,50-37)35(45)14-13-25(4)17-30(29)41(31,22-34(28)44)38(47)49-9/h12,17-18,23,28,30-31,35-37,45-46,48H,10-11,13-16,19-22H2,1-9H3/b24-18+,25-17+,26-12+/t28-,30-,31+,35-,36-,37+,39-,40-,41-/m0/s1
SMILES:	CC(C)[C@@H]1CC(=O)/C(=C/CC/C(=C/C(=O)[C@H]2CC(=C3C[C@@H]([C@@](C)([C@H]4CC[C@@](C)([C@H](CC/C(=C/[C@@H]3[C@]2(CC1=O)C(=O)OC)/C)O)O4)O)O)C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564585
PubChem CID:	44140534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0000357] Sesquaterpenoids

*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
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332846]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	Amami Oshima, Kagoshima Prefecture, Japan	n.a.	PMID[16933862]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331379]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21563811]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	58000.0	nM	PMID[554462]

☑ 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 NPC101067 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	203
0.1-0.2	1166
0.2-0.3	4957
0.3-0.4	11127
0.4-0.5	11159
0.5-0.6	6728
0.6-0.7	6050
0.7-0.8	1282
0.8-0.85	15
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476134
0.9479	High Similarity	NPC476235
0.9479	High Similarity	NPC476126
0.9375	High Similarity	NPC476213
0.9375	High Similarity	NPC477870
0.9375	High Similarity	NPC476246
0.9375	High Similarity	NPC477871
0.9062	High Similarity	NPC124246
0.8889	High Similarity	NPC283567
0.88	High Similarity	NPC475321
0.8529	High Similarity	NPC470104
0.8173	Intermediate Similarity	NPC255309
0.8137	Intermediate Similarity	NPC167974
0.8131	Intermediate Similarity	NPC286880
0.8131	Intermediate Similarity	NPC5284
0.8095	Intermediate Similarity	NPC96377
0.8095	Intermediate Similarity	NPC471332
0.8095	Intermediate Similarity	NPC471333
0.8095	Intermediate Similarity	NPC102352
0.8077	Intermediate Similarity	NPC69171
0.8077	Intermediate Similarity	NPC474165
0.8061	Intermediate Similarity	NPC478003
0.8061	Intermediate Similarity	NPC478004
0.8061	Intermediate Similarity	NPC158388
0.8041	Intermediate Similarity	NPC309656
0.8039	Intermediate Similarity	NPC471331
0.8039	Intermediate Similarity	NPC99657
0.8039	Intermediate Similarity	NPC203388
0.8039	Intermediate Similarity	NPC471330
0.8039	Intermediate Similarity	NPC222303
0.8039	Intermediate Similarity	NPC472687
0.8037	Intermediate Similarity	NPC153239
0.802	Intermediate Similarity	NPC8803
0.8	Intermediate Similarity	NPC114162
0.8	Intermediate Similarity	NPC146731
0.8	Intermediate Similarity	NPC296950
0.8	Intermediate Similarity	NPC469819
0.8	Intermediate Similarity	NPC472756
0.7981	Intermediate Similarity	NPC183571
0.7981	Intermediate Similarity	NPC473163
0.7963	Intermediate Similarity	NPC5103
0.7961	Intermediate Similarity	NPC472727
0.7961	Intermediate Similarity	NPC472728
0.7946	Intermediate Similarity	NPC234522
0.7944	Intermediate Similarity	NPC19412
0.7944	Intermediate Similarity	NPC154608
0.7944	Intermediate Similarity	NPC277017
0.7944	Intermediate Similarity	NPC192813
0.7941	Intermediate Similarity	NPC27105
0.7928	Intermediate Similarity	NPC40632
0.7928	Intermediate Similarity	NPC251236
0.7928	Intermediate Similarity	NPC328374
0.7928	Intermediate Similarity	NPC96312
0.7909	Intermediate Similarity	NPC469463
0.7909	Intermediate Similarity	NPC469496
0.7909	Intermediate Similarity	NPC49451
0.7909	Intermediate Similarity	NPC469454
0.79	Intermediate Similarity	NPC477615
0.7885	Intermediate Similarity	NPC115862
0.7885	Intermediate Similarity	NPC97435
0.787	Intermediate Similarity	NPC304495
0.7864	Intermediate Similarity	NPC23364
0.7864	Intermediate Similarity	NPC177680
0.7864	Intermediate Similarity	NPC153776
0.7864	Intermediate Similarity	NPC472729
0.7864	Intermediate Similarity	NPC472730
0.7857	Intermediate Similarity	NPC476706
0.7857	Intermediate Similarity	NPC472934
0.7857	Intermediate Similarity	NPC476707
0.7857	Intermediate Similarity	NPC476708
0.785	Intermediate Similarity	NPC144854
0.785	Intermediate Similarity	NPC67321
0.785	Intermediate Similarity	NPC3316
0.785	Intermediate Similarity	NPC187435
0.785	Intermediate Similarity	NPC293512
0.7843	Intermediate Similarity	NPC471775
0.7838	Intermediate Similarity	NPC473798
0.783	Intermediate Similarity	NPC471293
0.783	Intermediate Similarity	NPC65523
0.7818	Intermediate Similarity	NPC236217
0.7818	Intermediate Similarity	NPC474516
0.7818	Intermediate Similarity	NPC152117
0.7818	Intermediate Similarity	NPC472002
0.7818	Intermediate Similarity	NPC234042
0.781	Intermediate Similarity	NPC473928
0.78	Intermediate Similarity	NPC184463
0.7798	Intermediate Similarity	NPC474567
0.7798	Intermediate Similarity	NPC235014
0.7798	Intermediate Similarity	NPC210005
0.7798	Intermediate Similarity	NPC473627
0.7788	Intermediate Similarity	NPC106644
0.7788	Intermediate Similarity	NPC17772
0.7788	Intermediate Similarity	NPC241221
0.7778	Intermediate Similarity	NPC151393
0.7778	Intermediate Similarity	NPC306265
0.7778	Intermediate Similarity	NPC473288
0.7778	Intermediate Similarity	NPC168131
0.7778	Intermediate Similarity	NPC477973
0.7778	Intermediate Similarity	NPC258323
0.7768	Intermediate Similarity	NPC152199
0.7768	Intermediate Similarity	NPC134869
0.7768	Intermediate Similarity	NPC207217
0.7768	Intermediate Similarity	NPC235539
0.7767	Intermediate Similarity	NPC472732
0.7767	Intermediate Similarity	NPC472731
0.7757	Intermediate Similarity	NPC477125
0.7757	Intermediate Similarity	NPC181357
0.7757	Intermediate Similarity	NPC253223
0.7757	Intermediate Similarity	NPC472935
0.7748	Intermediate Similarity	NPC255017
0.7748	Intermediate Similarity	NPC471204
0.7745	Intermediate Similarity	NPC36954
0.7745	Intermediate Similarity	NPC183012
0.7745	Intermediate Similarity	NPC108141
0.7736	Intermediate Similarity	NPC472755
0.7736	Intermediate Similarity	NPC8196
0.7736	Intermediate Similarity	NPC475873
0.7736	Intermediate Similarity	NPC239716
0.7736	Intermediate Similarity	NPC270046
0.7736	Intermediate Similarity	NPC4620
0.7736	Intermediate Similarity	NPC264048
0.7736	Intermediate Similarity	NPC478057
0.7736	Intermediate Similarity	NPC99266
0.7732	Intermediate Similarity	NPC329738
0.7727	Intermediate Similarity	NPC188738
0.7727	Intermediate Similarity	NPC324683
0.7727	Intermediate Similarity	NPC304180
0.7727	Intermediate Similarity	NPC179798
0.7723	Intermediate Similarity	NPC476300
0.7719	Intermediate Similarity	NPC472933
0.7719	Intermediate Similarity	NPC470777
0.7714	Intermediate Similarity	NPC476270
0.7706	Intermediate Similarity	NPC41405
0.7706	Intermediate Similarity	NPC475922
0.7706	Intermediate Similarity	NPC310546
0.7699	Intermediate Similarity	NPC97908
0.7699	Intermediate Similarity	NPC474654
0.7699	Intermediate Similarity	NPC470854
0.7699	Intermediate Similarity	NPC122033
0.7699	Intermediate Similarity	NPC287343
0.7692	Intermediate Similarity	NPC216478
0.7692	Intermediate Similarity	NPC70733
0.7692	Intermediate Similarity	NPC56071
0.7685	Intermediate Similarity	NPC59530
0.7685	Intermediate Similarity	NPC230541
0.7685	Intermediate Similarity	NPC143609
0.7684	Intermediate Similarity	NPC327002
0.7679	Intermediate Similarity	NPC474181
0.7679	Intermediate Similarity	NPC18547
0.7679	Intermediate Similarity	NPC474906
0.7679	Intermediate Similarity	NPC472400
0.767	Intermediate Similarity	NPC472734
0.767	Intermediate Similarity	NPC472675
0.767	Intermediate Similarity	NPC256230
0.767	Intermediate Similarity	NPC21681
0.767	Intermediate Similarity	NPC472733
0.7664	Intermediate Similarity	NPC475676
0.7664	Intermediate Similarity	NPC472748
0.7664	Intermediate Similarity	NPC220964
0.7664	Intermediate Similarity	NPC258532
0.7658	Intermediate Similarity	NPC280782
0.7658	Intermediate Similarity	NPC470063
0.7658	Intermediate Similarity	NPC11252
0.7658	Intermediate Similarity	NPC317687
0.7658	Intermediate Similarity	NPC269530
0.7658	Intermediate Similarity	NPC289312
0.7647	Intermediate Similarity	NPC318332
0.7642	Intermediate Similarity	NPC324017
0.7642	Intermediate Similarity	NPC281702
0.7642	Intermediate Similarity	NPC293753
0.7642	Intermediate Similarity	NPC223834
0.7642	Intermediate Similarity	NPC234892
0.7642	Intermediate Similarity	NPC476081
0.7642	Intermediate Similarity	NPC137430
0.7642	Intermediate Similarity	NPC472754
0.7642	Intermediate Similarity	NPC320019
0.7636	Intermediate Similarity	NPC29133
0.7636	Intermediate Similarity	NPC161816
0.7636	Intermediate Similarity	NPC115257
0.7636	Intermediate Similarity	NPC37116
0.7632	Intermediate Similarity	NPC146280
0.7632	Intermediate Similarity	NPC297179
0.7632	Intermediate Similarity	NPC124676
0.7624	Intermediate Similarity	NPC252433
0.7624	Intermediate Similarity	NPC208839
0.7624	Intermediate Similarity	NPC30515
0.7624	Intermediate Similarity	NPC303697
0.7624	Intermediate Similarity	NPC476705
0.7615	Intermediate Similarity	NPC55972
0.7615	Intermediate Similarity	NPC327286
0.7615	Intermediate Similarity	NPC472439
0.7615	Intermediate Similarity	NPC169888
0.7615	Intermediate Similarity	NPC293850
0.7615	Intermediate Similarity	NPC469916
0.7611	Intermediate Similarity	NPC270478
0.7611	Intermediate Similarity	NPC148458
0.76	Intermediate Similarity	NPC269267
0.76	Intermediate Similarity	NPC307411
0.76	Intermediate Similarity	NPC5509
0.7596	Intermediate Similarity	NPC111348

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 NPC101067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1828
0.2-0.3	3809
0.3-0.4	2231
0.4-0.5	630
0.5-0.6	256
0.6-0.7	202
0.7-0.8	13
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
0.7549	Intermediate Similarity	NPD6399	Phase 3
0.7524	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7455	Intermediate Similarity	NPD6686	Approved
0.7429	Intermediate Similarity	NPD6083	Phase 2
0.7429	Intermediate Similarity	NPD6084	Phase 2
0.7429	Intermediate Similarity	NPD7902	Approved
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6649	Approved
0.7391	Intermediate Similarity	NPD7115	Discovery
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD6412	Phase 2
0.7364	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4225	Approved
0.7353	Intermediate Similarity	NPD6698	Approved
0.7353	Intermediate Similarity	NPD46	Approved
0.7321	Intermediate Similarity	NPD6371	Approved
0.7308	Intermediate Similarity	NPD7748	Approved
0.7238	Intermediate Similarity	NPD5210	Approved
0.7238	Intermediate Similarity	NPD4629	Approved
0.7238	Intermediate Similarity	NPD5695	Phase 3
0.7232	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.7143	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7129	Intermediate Similarity	NPD7521	Approved
0.7129	Intermediate Similarity	NPD7334	Approved
0.7129	Intermediate Similarity	NPD6684	Approved
0.7129	Intermediate Similarity	NPD7146	Approved
0.7129	Intermediate Similarity	NPD6409	Approved
0.7129	Intermediate Similarity	NPD5330	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD7515	Phase 2
0.7105	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5697	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7019	Intermediate Similarity	NPD7838	Discovery
0.7018	Intermediate Similarity	NPD7290	Approved
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6672	Approved
0.699	Remote Similarity	NPD5737	Approved
0.699	Remote Similarity	NPD6903	Approved
0.699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7492	Approved
0.6964	Remote Similarity	NPD6008	Approved
0.6961	Remote Similarity	NPD3618	Phase 1
0.6957	Remote Similarity	NPD6847	Approved
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD6869	Approved
0.6952	Remote Similarity	NPD6411	Approved
0.6952	Remote Similarity	NPD7983	Approved
0.6935	Remote Similarity	NPD7736	Approved
0.6931	Remote Similarity	NPD4786	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4753	Phase 2
0.6917	Remote Similarity	NPD6054	Approved
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6616	Approved
0.6903	Remote Similarity	NPD5701	Approved
0.69	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.6881	Remote Similarity	NPD7638	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1694	Approved
0.6857	Remote Similarity	NPD5785	Approved
0.6855	Remote Similarity	NPD8293	Discontinued
0.6855	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD6011	Approved
0.6818	Remote Similarity	NPD7639	Approved
0.6818	Remote Similarity	NPD7640	Approved
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6009	Approved
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD5369	Approved
0.6792	Remote Similarity	NPD5284	Approved
0.6792	Remote Similarity	NPD6079	Approved
0.6792	Remote Similarity	NPD5281	Approved
0.6777	Remote Similarity	NPD6059	Approved
0.6772	Remote Similarity	NPD7260	Phase 2
0.6762	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD6673	Approved
0.6762	Remote Similarity	NPD5328	Approved
0.6762	Remote Similarity	NPD6904	Approved
0.6762	Remote Similarity	NPD6080	Approved
0.6762	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6053	Discontinued
0.6748	Remote Similarity	NPD7604	Phase 2
0.6733	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD5983	Phase 2
0.6721	Remote Similarity	NPD6016	Approved
0.67	Remote Similarity	NPD4695	Discontinued
0.6699	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5363	Approved
0.6698	Remote Similarity	NPD5207	Approved
0.6697	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7507	Approved
0.664	Remote Similarity	NPD6336	Discontinued
0.6636	Remote Similarity	NPD8035	Phase 2
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD6050	Approved
0.6635	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5279	Phase 3
0.6607	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD6845	Suspended
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6583	Remote Similarity	NPD6274	Approved
0.6574	Remote Similarity	NPD4202	Approved
0.6571	Remote Similarity	NPD3573	Approved
0.6571	Remote Similarity	NPD7524	Approved
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6569	Remote Similarity	NPD6435	Approved
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD8133	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5225	Approved
0.6549	Remote Similarity	NPD5224	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6549	Remote Similarity	NPD4633	Approved
0.6545	Remote Similarity	NPD5222	Approved
0.6545	Remote Similarity	NPD7732	Phase 3
0.6545	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5221	Approved
0.6545	Remote Similarity	NPD7614	Phase 1
0.6542	Remote Similarity	NPD5692	Phase 3
0.6538	Remote Similarity	NPD5329	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6514	Remote Similarity	NPD6001	Approved
0.6509	Remote Similarity	NPD5208	Approved
0.6505	Remote Similarity	NPD7154	Phase 3
0.65	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5175	Approved
0.6491	Remote Similarity	NPD5174	Approved
0.6486	Remote Similarity	NPD5173	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD7637	Suspended
0.6481	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD5694	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD5786	Approved
0.6476	Remote Similarity	NPD6098	Approved
0.6475	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD6614	Approved
0.646	Remote Similarity	NPD5223	Approved
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7503	Approved
0.6452	Remote Similarity	NPD8033	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6446	Remote Similarity	NPD6868	Approved
0.6442	Remote Similarity	NPD3668	Phase 3
0.6442	Remote Similarity	NPD4197	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.641	Remote Similarity	NPD4729	Approved
0.641	Remote Similarity	NPD4730	Approved
0.6408	Remote Similarity	NPD4269	Approved
0.6408	Remote Similarity	NPD4270	Approved
0.6396	Remote Similarity	NPD7839	Suspended
0.6393	Remote Similarity	NPD6317	Approved
0.6379	Remote Similarity	NPD4768	Approved
0.6379	Remote Similarity	NPD4767	Approved
0.6373	Remote Similarity	NPD5368	Approved
0.6373	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD8294	Approved
0.6371	Remote Similarity	NPD8377	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