NPASS Compound

Structure

NPC36954 OpenBabel07101719522D 32 33 0 0 1 0 0 0 0 0999 V2000 6.2239 1.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0290 -1.8345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6885 2.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3595 5.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5880 4.9267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2518 -0.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5144 2.9154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9320 0.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0777 2.0891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3209 -0.9537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6483 3.4154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0401 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 4.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2267 1.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3237 -0.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2412 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3706 5.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5908 4.8520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7453 1.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7203 3.1248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4577 -0.3789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8944 0.4473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7018 0.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6511 3.4901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7472 6.2827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0275 5.6782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7775 -1.1120 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 0.5633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0276 4.2719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0053 4.5700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1569 3.9510 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 11 24 1 0 0 0 0 12 20 1 0 0 0 0 13 24 1 0 0 0 0 13 30 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 16 23 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 12 1 1 0 0 0 19 22 1 0 0 0 0 20 24 1 6 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 32 1 6 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.23
Volume:	461.05
LogP:	2.117
LogD:	1.744
LogS:	-3.951
# Rotatable Bonds:	5
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	5.136
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.91
MDCK Permeability:	7.706810720264912e-05
Pgp-inhibitor:	0.782
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	81.8087387084961%
Volume Distribution (VD):	0.698
Pgp-substrate:	20.681854248046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	2.846
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.938
Carcinogencity:	0.021
Eye Corrosion:	0.012
Eye Irritation:	0.059
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC36954

Natural Product ID:	NPC36954
*Common Name:**	Durumolide G
IUPAC Name:	[(3aR,5S,6S,9E,13E,15R,15aR)-5-acetyloxy-6,15-dihydroxy-10,14-dimethyl-3-methylidene-2-oxo-4,5,7,8,11,12,15,15a-octahydro-3aH-cyclotetradeca[b]furan-6-yl]methyl acetate
Synonyms:	durumolide G
Standard InCHIKey:	KOXLNTVHCAHJPE-AVGSJBJPSA-N
Standard InCHI:	InChI=1S/C24H34O8/c1-14-8-6-10-15(2)21(27)22-19(16(3)23(28)32-22)12-20(31-18(5)26)24(29,11-7-9-14)13-30-17(4)25/h9-10,19-22,27,29H,3,6-8,11-13H2,1-2,4-5H3/b14-9+,15-10+/t19-,20+,21-,22-,24+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2C(=C)C(=O)O[C@H]2[C@H](O)/C(=C/CC/C(=C/CC[C@]1(O)COC(=O)C)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556102
PubChem CID:	45271265
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones [CHEMONTID:0002502] Cembranolides

*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
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO5325	Lobophytum durum	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	7.3	%	PMID[535961]

☑ 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 NPC36954 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	200
0.1-0.2	1197
0.2-0.3	4202
0.3-0.4	7350
0.4-0.5	14834
0.5-0.6	8112
0.6-0.7	4736
0.7-0.8	1595
0.8-0.85	352
0.85-0.9	86
0.9-0.95	25
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC475912
0.9773	High Similarity	NPC476300
0.9667	High Similarity	NPC476315
0.9659	High Similarity	NPC184463
0.9659	High Similarity	NPC30515
0.9556	High Similarity	NPC14961
0.9556	High Similarity	NPC270013
0.9545	High Similarity	NPC476004
0.9545	High Similarity	NPC51004
0.9545	High Similarity	NPC474761
0.9444	High Similarity	NPC474035
0.9444	High Similarity	NPC81386
0.9432	High Similarity	NPC307411
0.9333	High Similarity	NPC212486
0.9333	High Similarity	NPC179746
0.9333	High Similarity	NPC81419
0.9318	High Similarity	NPC202672
0.9222	High Similarity	NPC12172
0.9222	High Similarity	NPC208886
0.9111	High Similarity	NPC475748
0.9032	High Similarity	NPC279621
0.9022	High Similarity	NPC57405
0.9022	High Similarity	NPC303942
0.9011	High Similarity	NPC473321
0.9	High Similarity	NPC92974
0.9	High Similarity	NPC474032
0.8977	High Similarity	NPC137033
0.8977	High Similarity	NPC21469
0.8947	High Similarity	NPC288876
0.8936	High Similarity	NPC40812
0.8925	High Similarity	NPC471142
0.8913	High Similarity	NPC295204
0.8913	High Similarity	NPC288240
0.8913	High Similarity	NPC162205
0.8913	High Similarity	NPC273579
0.8901	High Similarity	NPC473619
0.8889	High Similarity	NPC474471
0.8889	High Similarity	NPC177629
0.8889	High Similarity	NPC58219
0.8889	High Similarity	NPC227379
0.8889	High Similarity	NPC153805
0.8889	High Similarity	NPC473715
0.8866	High Similarity	NPC472755
0.8864	High Similarity	NPC474780
0.8864	High Similarity	NPC151176
0.8864	High Similarity	NPC475963
0.8864	High Similarity	NPC3464
0.8842	High Similarity	NPC471144
0.8842	High Similarity	NPC187268
0.8842	High Similarity	NPC474213
0.8842	High Similarity	NPC473326
0.883	High Similarity	NPC473859
0.8817	High Similarity	NPC474247
0.8791	High Similarity	NPC295312
0.8778	High Similarity	NPC248602
0.8778	High Similarity	NPC231889
0.8778	High Similarity	NPC186148
0.8776	High Similarity	NPC100487
0.8763	High Similarity	NPC324017
0.8763	High Similarity	NPC320019
0.8763	High Similarity	NPC149371
0.875	High Similarity	NPC11620
0.8723	High Similarity	NPC475659
0.871	High Similarity	NPC125674
0.871	High Similarity	NPC475838
0.871	High Similarity	NPC228451
0.8696	High Similarity	NPC475855
0.8696	High Similarity	NPC473448
0.8687	High Similarity	NPC243998
0.8687	High Similarity	NPC223450
0.8673	High Similarity	NPC475871
0.8673	High Similarity	NPC475945
0.8667	High Similarity	NPC475019
0.8667	High Similarity	NPC474949
0.8667	High Similarity	NPC476015
0.8667	High Similarity	NPC474762
0.866	High Similarity	NPC476270
0.866	High Similarity	NPC15993
0.866	High Similarity	NPC47880
0.8646	High Similarity	NPC255592
0.8646	High Similarity	NPC83895
0.8646	High Similarity	NPC261377
0.8646	High Similarity	NPC187761
0.8646	High Similarity	NPC308567
0.8632	High Similarity	NPC230800
0.8632	High Similarity	NPC470883
0.8632	High Similarity	NPC477921
0.8632	High Similarity	NPC158416
0.8632	High Similarity	NPC76862
0.8632	High Similarity	NPC39859
0.8617	High Similarity	NPC71589
0.8617	High Similarity	NPC190294
0.86	High Similarity	NPC477513
0.8587	High Similarity	NPC477011
0.8587	High Similarity	NPC151770
0.8571	High Similarity	NPC472754
0.8571	High Similarity	NPC179659
0.8571	High Similarity	NPC86077
0.8571	High Similarity	NPC474747
0.8557	High Similarity	NPC475949
0.8556	High Similarity	NPC149725
0.8556	High Similarity	NPC329749
0.8556	High Similarity	NPC47958
0.8556	High Similarity	NPC255307
0.8556	High Similarity	NPC304509
0.8542	High Similarity	NPC328562
0.8542	High Similarity	NPC323421
0.8539	High Similarity	NPC250315
0.8526	High Similarity	NPC471141
0.8526	High Similarity	NPC477922
0.8526	High Similarity	NPC304886
0.85	High Similarity	NPC472751
0.85	High Similarity	NPC472749
0.8495	Intermediate Similarity	NPC179394
0.8495	Intermediate Similarity	NPC474232
0.8495	Intermediate Similarity	NPC144133
0.8478	Intermediate Similarity	NPC280621
0.8478	Intermediate Similarity	NPC281516
0.8478	Intermediate Similarity	NPC40376
0.8478	Intermediate Similarity	NPC48338
0.8478	Intermediate Similarity	NPC20339
0.8478	Intermediate Similarity	NPC89001
0.8478	Intermediate Similarity	NPC21208
0.8478	Intermediate Similarity	NPC233551
0.8469	Intermediate Similarity	NPC110443
0.8469	Intermediate Similarity	NPC150923
0.8469	Intermediate Similarity	NPC473332
0.8469	Intermediate Similarity	NPC46998
0.8469	Intermediate Similarity	NPC128733
0.8469	Intermediate Similarity	NPC472753
0.8469	Intermediate Similarity	NPC133907
0.8469	Intermediate Similarity	NPC474742
0.8469	Intermediate Similarity	NPC185141
0.8462	Intermediate Similarity	NPC112685
0.8462	Intermediate Similarity	NPC164393
0.8462	Intermediate Similarity	NPC305475
0.8462	Intermediate Similarity	NPC475461
0.8444	Intermediate Similarity	NPC70424
0.8444	Intermediate Similarity	NPC114979
0.8444	Intermediate Similarity	NPC9868
0.8444	Intermediate Similarity	NPC243618
0.8444	Intermediate Similarity	NPC191476
0.8438	Intermediate Similarity	NPC31645
0.8438	Intermediate Similarity	NPC476009
0.8421	Intermediate Similarity	NPC473316
0.8421	Intermediate Similarity	NPC474338
0.8421	Intermediate Similarity	NPC473330
0.8404	Intermediate Similarity	NPC470373
0.8404	Intermediate Similarity	NPC70251
0.8404	Intermediate Similarity	NPC470379
0.8404	Intermediate Similarity	NPC475881
0.84	Intermediate Similarity	NPC472748
0.84	Intermediate Similarity	NPC475676
0.84	Intermediate Similarity	NPC472756
0.84	Intermediate Similarity	NPC203659
0.84	Intermediate Similarity	NPC220964
0.84	Intermediate Similarity	NPC474741
0.8387	Intermediate Similarity	NPC280612
0.8387	Intermediate Similarity	NPC166919
0.8387	Intermediate Similarity	NPC473564
0.8387	Intermediate Similarity	NPC477016
0.8387	Intermediate Similarity	NPC477017
0.8384	Intermediate Similarity	NPC471148
0.837	Intermediate Similarity	NPC160138
0.837	Intermediate Similarity	NPC178215
0.8352	Intermediate Similarity	NPC165162
0.835	Intermediate Similarity	NPC5103
0.8333	Intermediate Similarity	NPC473390
0.8333	Intermediate Similarity	NPC272814
0.8333	Intermediate Similarity	NPC107476
0.8333	Intermediate Similarity	NPC475900
0.8333	Intermediate Similarity	NPC131669
0.8316	Intermediate Similarity	NPC469692
0.8316	Intermediate Similarity	NPC469645
0.8316	Intermediate Similarity	NPC11456
0.83	Intermediate Similarity	NPC472750
0.83	Intermediate Similarity	NPC110989
0.83	Intermediate Similarity	NPC472747
0.83	Intermediate Similarity	NPC4620
0.83	Intermediate Similarity	NPC69171
0.83	Intermediate Similarity	NPC474165
0.8298	Intermediate Similarity	NPC239517
0.8298	Intermediate Similarity	NPC474323
0.8298	Intermediate Similarity	NPC177668
0.8298	Intermediate Similarity	NPC473904
0.8298	Intermediate Similarity	NPC313670
0.8298	Intermediate Similarity	NPC206614
0.8286	Intermediate Similarity	NPC469463
0.8286	Intermediate Similarity	NPC469454
0.8286	Intermediate Similarity	NPC469496
0.8283	Intermediate Similarity	NPC201718
0.8283	Intermediate Similarity	NPC474339
0.8283	Intermediate Similarity	NPC164598
0.828	Intermediate Similarity	NPC476803
0.8261	Intermediate Similarity	NPC62118
0.8261	Intermediate Similarity	NPC475581
0.8261	Intermediate Similarity	NPC171174
0.8261	Intermediate Similarity	NPC114694
0.8261	Intermediate Similarity	NPC134865
0.8261	Intermediate Similarity	NPC232555

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 NPC36954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1754
0.2-0.3	3600
0.3-0.4	2295
0.4-0.5	845
0.5-0.6	326
0.6-0.7	110
0.7-0.8	28
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8495	Intermediate Similarity	NPD6698	Approved
0.8495	Intermediate Similarity	NPD46	Approved
0.8404	Intermediate Similarity	NPD7983	Approved
0.8235	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8152	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD7838	Discovery
0.8	Intermediate Similarity	NPD6371	Approved
0.7925	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6686	Approved
0.76	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8513	Phase 3
0.7456	Intermediate Similarity	NPD8516	Approved
0.7456	Intermediate Similarity	NPD8515	Approved
0.7456	Intermediate Similarity	NPD8517	Approved
0.7449	Intermediate Similarity	NPD1695	Approved
0.7404	Intermediate Similarity	NPD5344	Discontinued
0.74	Intermediate Similarity	NPD5778	Approved
0.74	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD4225	Approved
0.7368	Intermediate Similarity	NPD7154	Phase 3
0.7245	Intermediate Similarity	NPD4251	Approved
0.7245	Intermediate Similarity	NPD4250	Approved
0.7207	Intermediate Similarity	NPD6053	Discontinued
0.72	Intermediate Similarity	NPD5785	Approved
0.7184	Intermediate Similarity	NPD7839	Suspended
0.7143	Intermediate Similarity	NPD5786	Approved
0.7143	Intermediate Similarity	NPD8074	Phase 3
0.7143	Intermediate Similarity	NPD4249	Approved
0.7083	Intermediate Similarity	NPD6435	Approved
0.7053	Intermediate Similarity	NPD4822	Approved
0.7053	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4821	Approved
0.7053	Intermediate Similarity	NPD4819	Approved
0.7053	Intermediate Similarity	NPD4820	Approved
0.7041	Intermediate Similarity	NPD5363	Approved
0.701	Intermediate Similarity	NPD5362	Discontinued
0.6981	Remote Similarity	NPD6648	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6917	Remote Similarity	NPD7507	Approved
0.6907	Remote Similarity	NPD4269	Approved
0.6907	Remote Similarity	NPD4270	Approved
0.6891	Remote Similarity	NPD7642	Approved
0.6875	Remote Similarity	NPD5368	Approved
0.6869	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4271	Approved
0.6842	Remote Similarity	NPD4268	Approved
0.6827	Remote Similarity	NPD5282	Discontinued
0.6822	Remote Similarity	NPD7639	Approved
0.6822	Remote Similarity	NPD7640	Approved
0.6804	Remote Similarity	NPD5369	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8451	Approved
0.6772	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6101	Approved
0.6765	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7641	Discontinued
0.675	Remote Similarity	NPD7830	Approved
0.675	Remote Similarity	NPD7829	Approved
0.6748	Remote Similarity	NPD7319	Approved
0.6729	Remote Similarity	NPD7638	Approved
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8448	Approved
0.6701	Remote Similarity	NPD4252	Approved
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8340	Approved
0.6694	Remote Similarity	NPD8299	Approved
0.6694	Remote Similarity	NPD8341	Approved
0.6694	Remote Similarity	NPD8342	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6110	Phase 1
0.6639	Remote Similarity	NPD8273	Phase 1
0.6639	Remote Similarity	NPD6319	Approved
0.6635	Remote Similarity	NPD6411	Approved
0.6609	Remote Similarity	NPD8297	Approved
0.6583	Remote Similarity	NPD8444	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8392	Approved
0.656	Remote Similarity	NPD8391	Approved
0.656	Remote Similarity	NPD8390	Approved
0.6552	Remote Similarity	NPD4632	Approved
0.6535	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD6649	Approved
0.6522	Remote Similarity	NPD6650	Approved
0.6508	Remote Similarity	NPD7260	Phase 2
0.65	Remote Similarity	NPD5331	Approved
0.65	Remote Similarity	NPD5332	Approved
0.6491	Remote Similarity	NPD6373	Approved
0.6491	Remote Similarity	NPD6372	Approved
0.6484	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7637	Suspended
0.6465	Remote Similarity	NPD4790	Discontinued
0.646	Remote Similarity	NPD6412	Phase 2
0.646	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6421	Discontinued
0.6423	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD6399	Phase 3
0.641	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD7524	Approved
0.6404	Remote Similarity	NPD6881	Approved
0.6404	Remote Similarity	NPD6899	Approved
0.6387	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6402	Approved
0.6372	Remote Similarity	NPD5739	Approved
0.6372	Remote Similarity	NPD6008	Approved
0.6372	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD6675	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6341	Remote Similarity	NPD8328	Phase 3
0.6333	Remote Similarity	NPD7327	Approved
0.6333	Remote Similarity	NPD7328	Approved
0.6328	Remote Similarity	NPD6845	Suspended
0.6325	Remote Similarity	NPD6882	Approved
0.632	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD7503	Approved
0.6311	Remote Similarity	NPD8033	Approved
0.6293	Remote Similarity	NPD7290	Approved
0.6293	Remote Similarity	NPD7102	Approved
0.6293	Remote Similarity	NPD6883	Approved
0.6286	Remote Similarity	NPD5370	Suspended
0.6281	Remote Similarity	NPD7516	Approved
0.6275	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7736	Approved
0.6264	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7320	Approved
0.626	Remote Similarity	NPD8080	Discontinued
0.626	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7500	Approved
0.625	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD2204	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6869	Approved
0.6238	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6059	Approved
0.623	Remote Similarity	NPD8294	Approved
0.623	Remote Similarity	NPD8377	Approved
0.621	Remote Similarity	NPD7604	Phase 2
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.6207	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7331	Phase 2
0.619	Remote Similarity	NPD8293	Discontinued
0.6186	Remote Similarity	NPD8039	Approved
0.6183	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6083	Phase 2
0.6182	Remote Similarity	NPD6084	Phase 2
0.6179	Remote Similarity	NPD8296	Approved
0.6179	Remote Similarity	NPD8335	Approved
0.6179	Remote Similarity	NPD8267	Approved
0.6179	Remote Similarity	NPD8266	Approved
0.6179	Remote Similarity	NPD6015	Approved
0.6179	Remote Similarity	NPD8379	Approved
0.6179	Remote Similarity	NPD8380	Approved
0.6179	Remote Similarity	NPD5983	Phase 2
0.6179	Remote Similarity	NPD8268	Approved
0.6179	Remote Similarity	NPD8269	Approved
0.6179	Remote Similarity	NPD6016	Approved
0.6179	Remote Similarity	NPD6921	Approved
0.6179	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8378	Approved
0.6176	Remote Similarity	NPD6695	Phase 3
0.6174	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6422	Discontinued
0.6154	Remote Similarity	NPD3197	Phase 1
0.6154	Remote Similarity	NPD7909	Approved
0.6129	Remote Similarity	NPD5988	Approved
0.6121	Remote Similarity	NPD6011	Approved
0.6116	Remote Similarity	NPD7505	Discontinued
0.6111	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD5211	Phase 2
0.6091	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7341	Phase 2
0.6078	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD4756	Discovery
0.6036	Remote Similarity	NPD7902	Approved
0.6017	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD5141	Approved
0.5985	Remote Similarity	NPD8415	Approved
0.5982	Remote Similarity	NPD5696	Approved
0.5966	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7750	Discontinued
0.5929	Remote Similarity	NPD4696	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5909	Remote Similarity	NPD7748	Approved
0.5902	Remote Similarity	NPD6274	Approved
0.5893	Remote Similarity	NPD4755	Approved
0.5887	Remote Similarity	NPD7100	Approved
0.5887	Remote Similarity	NPD7101	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