NPASS Compound

Structure

CID177826 OpenBabel06191715552D 22 23 0 0 1 0 0 0 0 0999 V2000 2.9568 2.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5254 0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9909 1.9659 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 13 1 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 19 1 1 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 3 1 6 0 0 0 18 4 1 6 0 0 0 19 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.22
Volume:	338.529
LogP:	3.339
LogD:	2.847
LogS:	-2.458
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	4.611
Fsp3:	0.789
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.485
MDCK Permeability:	2.2962220100453123e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	83.284423828125%
Volume Distribution (VD):	0.34
Pgp-substrate:	15.718017578125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.544
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.552
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	15.128
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.515
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.393
Skin Sensitization:	0.69
Carcinogencity:	0.536
Eye Corrosion:	0.951
Eye Irritation:	0.332
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC177826

Natural Product ID:	NPC177826
*Common Name:**	Tagalsin H
IUPAC Name:	2-[(1R,2S,4aS,6S,8aS)-2-acetyl-6-ethenyl-2,6,8a-trimethyl-3,4,4a,5,7,8-hexahydro-1H-naphthalen-1-yl]acetic acid
Synonyms:
Standard InCHIKey:	ZWZOZRNYABZXCN-JAQSECSASA-N
Standard InCHI:	InChI=1S/C19H30O3/c1-6-17(3)9-10-19(5)14(12-17)7-8-18(4,13(2)20)15(19)11-16(21)22/h6,14-15H,1,7-12H2,2-5H3,(H,21,22)/p-1/t14-,15-,17-,18+,19-/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@@]2(C)[C@@H](CC[C@](C)(C(=O)C)[C@@H]2CC(=O)[O-])C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2272137
PubChem CID:	11716476
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378377]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	the mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	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
EC50	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	EC50	=	285.4	ppm	PMID[464101]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	92.86	%	PMID[464101]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	73.72	%	PMID[464101]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	63.26	%	PMID[464101]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	49.12	%	PMID[464101]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	Activity	=	35.41	%	PMID[464101]

☑ 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 NPC177826 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	168
0.1-0.2	1642
0.2-0.3	8476
0.3-0.4	15230
0.4-0.5	7940
0.5-0.6	5924
0.6-0.7	2854
0.7-0.8	420
0.8-0.85	37
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8676	High Similarity	NPC469791
0.8571	High Similarity	NPC238991
0.8571	High Similarity	NPC302661
0.8553	High Similarity	NPC26139
0.8514	High Similarity	NPC104806
0.8493	Intermediate Similarity	NPC255168
0.8493	Intermediate Similarity	NPC18819
0.8493	Intermediate Similarity	NPC46610
0.8481	Intermediate Similarity	NPC224345
0.8378	Intermediate Similarity	NPC192540
0.8378	Intermediate Similarity	NPC201027
0.8378	Intermediate Similarity	NPC279666
0.831	Intermediate Similarity	NPC290445
0.831	Intermediate Similarity	NPC470956
0.831	Intermediate Similarity	NPC36616
0.8286	Intermediate Similarity	NPC103734
0.8267	Intermediate Similarity	NPC69143
0.8267	Intermediate Similarity	NPC20466
0.8243	Intermediate Similarity	NPC183503
0.8243	Intermediate Similarity	NPC162164
0.8243	Intermediate Similarity	NPC476046
0.8243	Intermediate Similarity	NPC3753
0.8243	Intermediate Similarity	NPC103958
0.8243	Intermediate Similarity	NPC251970
0.8243	Intermediate Similarity	NPC38426
0.8243	Intermediate Similarity	NPC161923
0.8243	Intermediate Similarity	NPC237591
0.8243	Intermediate Similarity	NPC283908
0.8243	Intermediate Similarity	NPC241854
0.8228	Intermediate Similarity	NPC102197
0.8158	Intermediate Similarity	NPC212661
0.8158	Intermediate Similarity	NPC74685
0.8158	Intermediate Similarity	NPC471035
0.8158	Intermediate Similarity	NPC165711
0.8133	Intermediate Similarity	NPC476844
0.8108	Intermediate Similarity	NPC36310
0.8108	Intermediate Similarity	NPC472813
0.8108	Intermediate Similarity	NPC330659
0.8108	Intermediate Similarity	NPC244708
0.8108	Intermediate Similarity	NPC161187
0.8082	Intermediate Similarity	NPC91369
0.8082	Intermediate Similarity	NPC235586
0.8052	Intermediate Similarity	NPC179028
0.8052	Intermediate Similarity	NPC476810
0.8052	Intermediate Similarity	NPC269543
0.8052	Intermediate Similarity	NPC247783
0.8026	Intermediate Similarity	NPC180886
0.7975	Intermediate Similarity	NPC263272
0.7975	Intermediate Similarity	NPC221647
0.7975	Intermediate Similarity	NPC471898
0.7975	Intermediate Similarity	NPC267691
0.7975	Intermediate Similarity	NPC278459
0.7975	Intermediate Similarity	NPC20096
0.7975	Intermediate Similarity	NPC274050
0.7975	Intermediate Similarity	NPC147066
0.7975	Intermediate Similarity	NPC48673
0.7975	Intermediate Similarity	NPC162632
0.7973	Intermediate Similarity	NPC472309
0.7973	Intermediate Similarity	NPC72343
0.7973	Intermediate Similarity	NPC160817
0.7949	Intermediate Similarity	NPC231431
0.7949	Intermediate Similarity	NPC192744
0.7949	Intermediate Similarity	NPC477371
0.7927	Intermediate Similarity	NPC6247
0.7922	Intermediate Similarity	NPC471897
0.7922	Intermediate Similarity	NPC471899
0.7922	Intermediate Similarity	NPC66105
0.7922	Intermediate Similarity	NPC107039
0.7922	Intermediate Similarity	NPC472746
0.7895	Intermediate Similarity	NPC39362
0.7875	Intermediate Similarity	NPC69101
0.7875	Intermediate Similarity	NPC251779
0.7848	Intermediate Similarity	NPC37038
0.7838	Intermediate Similarity	NPC163020
0.7831	Intermediate Similarity	NPC476409
0.7821	Intermediate Similarity	NPC110094
0.7821	Intermediate Similarity	NPC321514
0.7821	Intermediate Similarity	NPC260385
0.7821	Intermediate Similarity	NPC280654
0.7821	Intermediate Similarity	NPC321690
0.7821	Intermediate Similarity	NPC74410
0.7805	Intermediate Similarity	NPC142649
0.7805	Intermediate Similarity	NPC29447
0.7805	Intermediate Similarity	NPC474537
0.7792	Intermediate Similarity	NPC89294
0.7792	Intermediate Similarity	NPC309399
0.7792	Intermediate Similarity	NPC246445
0.7778	Intermediate Similarity	NPC70834
0.7778	Intermediate Similarity	NPC477852
0.7778	Intermediate Similarity	NPC105803
0.7763	Intermediate Similarity	NPC301065
0.775	Intermediate Similarity	NPC38350
0.775	Intermediate Similarity	NPC142244
0.775	Intermediate Similarity	NPC90055
0.775	Intermediate Similarity	NPC477372
0.775	Intermediate Similarity	NPC201912
0.7722	Intermediate Similarity	NPC199595
0.7722	Intermediate Similarity	NPC28319
0.7722	Intermediate Similarity	NPC158846
0.7722	Intermediate Similarity	NPC192329
0.7722	Intermediate Similarity	NPC263951
0.7722	Intermediate Similarity	NPC16394
0.7722	Intermediate Similarity	NPC474113
0.7692	Intermediate Similarity	NPC475932
0.7692	Intermediate Similarity	NPC238227
0.7692	Intermediate Similarity	NPC97377
0.7692	Intermediate Similarity	NPC61952
0.7692	Intermediate Similarity	NPC472300
0.7692	Intermediate Similarity	NPC68828
0.7692	Intermediate Similarity	NPC474433
0.7683	Intermediate Similarity	NPC96095
0.7674	Intermediate Similarity	NPC230064
0.7662	Intermediate Similarity	NPC472311
0.7662	Intermediate Similarity	NPC476795
0.7654	Intermediate Similarity	NPC73882
0.7654	Intermediate Similarity	NPC320514
0.7654	Intermediate Similarity	NPC123880
0.7654	Intermediate Similarity	NPC260956
0.7654	Intermediate Similarity	NPC133391
0.7654	Intermediate Similarity	NPC471159
0.7639	Intermediate Similarity	NPC230047
0.7639	Intermediate Similarity	NPC19311
0.7632	Intermediate Similarity	NPC321017
0.7625	Intermediate Similarity	NPC477057
0.7625	Intermediate Similarity	NPC469637
0.7625	Intermediate Similarity	NPC104545
0.7625	Intermediate Similarity	NPC476809
0.7595	Intermediate Similarity	NPC275494
0.7595	Intermediate Similarity	NPC239098
0.7595	Intermediate Similarity	NPC59436
0.7595	Intermediate Similarity	NPC198240
0.7595	Intermediate Similarity	NPC471409
0.759	Intermediate Similarity	NPC474680
0.759	Intermediate Similarity	NPC269638
0.759	Intermediate Similarity	NPC473038
0.7586	Intermediate Similarity	NPC131840
0.7568	Intermediate Similarity	NPC469724
0.7568	Intermediate Similarity	NPC31187
0.7568	Intermediate Similarity	NPC100917
0.7568	Intermediate Similarity	NPC281203
0.7564	Intermediate Similarity	NPC476601
0.7561	Intermediate Similarity	NPC472740
0.7561	Intermediate Similarity	NPC477373
0.7561	Intermediate Similarity	NPC312480
0.7561	Intermediate Similarity	NPC83569
0.7561	Intermediate Similarity	NPC69279
0.7561	Intermediate Similarity	NPC167103
0.7558	Intermediate Similarity	NPC476369
0.7558	Intermediate Similarity	NPC263977
0.7558	Intermediate Similarity	NPC476437
0.7532	Intermediate Similarity	NPC166797
0.7531	Intermediate Similarity	NPC474955
0.7531	Intermediate Similarity	NPC189237
0.7531	Intermediate Similarity	NPC327002
0.7531	Intermediate Similarity	NPC232625
0.7531	Intermediate Similarity	NPC473420
0.75	Intermediate Similarity	NPC215843
0.75	Intermediate Similarity	NPC229717
0.75	Intermediate Similarity	NPC327674
0.75	Intermediate Similarity	NPC82979
0.7471	Intermediate Similarity	NPC327515
0.747	Intermediate Similarity	NPC156981
0.7468	Intermediate Similarity	NPC149249
0.7468	Intermediate Similarity	NPC106078
0.7468	Intermediate Similarity	NPC476811
0.7442	Intermediate Similarity	NPC262043
0.7439	Intermediate Similarity	NPC100297
0.7439	Intermediate Similarity	NPC474605
0.7439	Intermediate Similarity	NPC170985
0.7439	Intermediate Similarity	NPC476292
0.7432	Intermediate Similarity	NPC263161
0.7432	Intermediate Similarity	NPC60120
0.7432	Intermediate Similarity	NPC41542
0.7412	Intermediate Similarity	NPC158141
0.7412	Intermediate Similarity	NPC136948
0.7412	Intermediate Similarity	NPC128644
0.7412	Intermediate Similarity	NPC173089
0.7412	Intermediate Similarity	NPC96496
0.7407	Intermediate Similarity	NPC267517
0.7407	Intermediate Similarity	NPC164999
0.7407	Intermediate Similarity	NPC2482
0.7403	Intermediate Similarity	NPC279241
0.7403	Intermediate Similarity	NPC35656
0.7381	Intermediate Similarity	NPC311702
0.7381	Intermediate Similarity	NPC94531
0.7381	Intermediate Similarity	NPC123319
0.7381	Intermediate Similarity	NPC76333
0.7381	Intermediate Similarity	NPC201655
0.7375	Intermediate Similarity	NPC63020
0.7368	Intermediate Similarity	NPC108131
0.7363	Intermediate Similarity	NPC474724
0.7349	Intermediate Similarity	NPC245866
0.7349	Intermediate Similarity	NPC107253
0.7349	Intermediate Similarity	NPC471037
0.7349	Intermediate Similarity	NPC215893
0.7349	Intermediate Similarity	NPC200752
0.7349	Intermediate Similarity	NPC49019
0.7342	Intermediate Similarity	NPC198473
0.7333	Intermediate Similarity	NPC269492
0.7326	Intermediate Similarity	NPC474511

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 NPC177826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	2208
0.2-0.3	4124
0.3-0.4	1763
0.4-0.5	475
0.5-0.6	243
0.6-0.7	155
0.7-0.8	14
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
0.7778	Intermediate Similarity	NPD4224	Phase 2
0.7733	Intermediate Similarity	NPD6081	Approved
0.7333	Intermediate Similarity	NPD7614	Phase 1
0.7241	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4221	Approved
0.7229	Intermediate Similarity	NPD4223	Phase 3
0.7229	Intermediate Similarity	NPD3667	Approved
0.7209	Intermediate Similarity	NPD3573	Approved
0.7195	Intermediate Similarity	NPD4695	Discontinued
0.7176	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3617	Approved
0.7093	Intermediate Similarity	NPD4623	Approved
0.7093	Intermediate Similarity	NPD4519	Discontinued
0.7079	Intermediate Similarity	NPD5284	Approved
0.7079	Intermediate Similarity	NPD5281	Approved
0.7079	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD4197	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3702	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD5696	Approved
0.6977	Remote Similarity	NPD5329	Approved
0.6957	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD4690	Approved
0.6897	Remote Similarity	NPD5690	Phase 2
0.6897	Remote Similarity	NPD3618	Phase 1
0.6897	Remote Similarity	NPD4693	Phase 3
0.6897	Remote Similarity	NPD4688	Approved
0.6897	Remote Similarity	NPD5205	Approved
0.6897	Remote Similarity	NPD6409	Approved
0.6897	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7521	Approved
0.6897	Remote Similarity	NPD7334	Approved
0.6897	Remote Similarity	NPD5330	Approved
0.6897	Remote Similarity	NPD4689	Approved
0.6897	Remote Similarity	NPD4138	Approved
0.6897	Remote Similarity	NPD6098	Approved
0.6897	Remote Similarity	NPD7146	Approved
0.6897	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD6079	Approved
0.6883	Remote Similarity	NPD5360	Phase 3
0.6883	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5328	Approved
0.6848	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD5210	Approved
0.6795	Remote Similarity	NPD3698	Phase 2
0.6795	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7732	Phase 3
0.6742	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5737	Approved
0.6742	Remote Similarity	NPD6672	Approved
0.6742	Remote Similarity	NPD6903	Approved
0.6742	Remote Similarity	NPD5208	Approved
0.6709	Remote Similarity	NPD4244	Approved
0.6709	Remote Similarity	NPD4245	Approved
0.6709	Remote Similarity	NPD4789	Approved
0.6707	Remote Similarity	NPD6117	Approved
0.6706	Remote Similarity	NPD4139	Approved
0.6706	Remote Similarity	NPD4692	Approved
0.6705	Remote Similarity	NPD5280	Approved
0.6705	Remote Similarity	NPD4694	Approved
0.6703	Remote Similarity	NPD8035	Phase 2
0.6703	Remote Similarity	NPD8034	Phase 2
0.6702	Remote Similarity	NPD7902	Approved
0.6702	Remote Similarity	NPD6083	Phase 2
0.6702	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6628	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6116	Phase 1
0.6625	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5777	Approved
0.6625	Remote Similarity	NPD4758	Discontinued
0.6625	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5221	Approved
0.6596	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5222	Approved
0.6593	Remote Similarity	NPD5207	Approved
0.6585	Remote Similarity	NPD3703	Phase 2
0.6582	Remote Similarity	NPD4137	Phase 3
0.6548	Remote Similarity	NPD6115	Approved
0.6548	Remote Similarity	NPD6118	Approved
0.6548	Remote Similarity	NPD6114	Approved
0.6548	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6697	Approved
0.6526	Remote Similarity	NPD5173	Approved
0.6522	Remote Similarity	NPD5694	Approved
0.6522	Remote Similarity	NPD5693	Phase 1
0.6522	Remote Similarity	NPD6411	Approved
0.6517	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD4747	Approved
0.65	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD4691	Approved
0.6494	Remote Similarity	NPD7341	Phase 2
0.6463	Remote Similarity	NPD4058	Approved
0.6456	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4202	Approved
0.6436	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6881	Approved
0.6436	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD5091	Approved
0.6421	Remote Similarity	NPD4697	Phase 3
0.6413	Remote Similarity	NPD5692	Phase 3
0.641	Remote Similarity	NPD7331	Phase 2
0.6404	Remote Similarity	NPD1694	Approved
0.64	Remote Similarity	NPD5739	Approved
0.64	Remote Similarity	NPD6402	Approved
0.64	Remote Similarity	NPD7128	Approved
0.64	Remote Similarity	NPD6675	Approved
0.6395	Remote Similarity	NPD5368	Approved
0.6392	Remote Similarity	NPD4696	Approved
0.6392	Remote Similarity	NPD5286	Approved
0.6392	Remote Similarity	NPD5285	Approved
0.6383	Remote Similarity	NPD6001	Approved
0.6383	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7900	Approved
0.6373	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD6012	Approved
0.6373	Remote Similarity	NPD6013	Approved
0.6354	Remote Similarity	NPD4755	Approved
0.6344	Remote Similarity	NPD6050	Approved
0.6338	Remote Similarity	NPD3172	Approved
0.6337	Remote Similarity	NPD5701	Approved
0.6327	Remote Similarity	NPD5223	Approved
0.6324	Remote Similarity	NPD622	Approved
0.6316	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD7290	Approved
0.6311	Remote Similarity	NPD6883	Approved
0.6304	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD5133	Approved
0.6275	Remote Similarity	NPD7320	Approved
0.6269	Remote Similarity	NPD634	Phase 3
0.6265	Remote Similarity	NPD4785	Approved
0.6265	Remote Similarity	NPD4687	Approved
0.6265	Remote Similarity	NPD4784	Approved
0.6263	Remote Similarity	NPD5225	Approved
0.6263	Remote Similarity	NPD4633	Approved
0.6263	Remote Similarity	NPD5224	Approved
0.6263	Remote Similarity	NPD5226	Approved
0.6263	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD4266	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.6237	Remote Similarity	NPD4096	Approved
0.6224	Remote Similarity	NPD4700	Approved
0.622	Remote Similarity	NPD4243	Approved
0.6214	Remote Similarity	NPD6372	Approved
0.6214	Remote Similarity	NPD6373	Approved
0.62	Remote Similarity	NPD5174	Approved
0.62	Remote Similarity	NPD5175	Approved
0.6196	Remote Similarity	NPD4518	Approved
0.619	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD6614	Approved
0.6163	Remote Similarity	NPD5364	Discontinued
0.6163	Remote Similarity	NPD3671	Phase 1
0.6146	Remote Similarity	NPD5654	Approved
0.6139	Remote Similarity	NPD5141	Approved
0.6136	Remote Similarity	NPD5369	Approved
0.6132	Remote Similarity	NPD4632	Approved
0.6122	Remote Similarity	NPD7638	Approved
0.6118	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD5778	Approved
0.6095	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5733	Approved
0.6067	Remote Similarity	NPD4270	Approved
0.6067	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD7639	Approved
0.6061	Remote Similarity	NPD7640	Approved
0.6061	Remote Similarity	NPD6404	Discontinued
0.604	Remote Similarity	NPD4754	Approved
0.6027	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5276	Approved
0.602	Remote Similarity	NPD5959	Approved
0.6019	Remote Similarity	NPD6868	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