NPASS Compound

Structure

NPC69171 OpenBabel07101718322D 32 34 0 0 1 0 0 0 0 0999 V2000 -0.9511 2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 0.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3479 -1.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6764 5.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6758 4.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 1.8749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6709 5.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 4.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 3.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9437 3.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0777 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 2.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2587 5.9586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8097 5.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0777 4.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 4.1180 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 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 7 9 1 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 1 0 0 0 15 25 2 0 0 0 0 15 30 1 0 0 0 0 16 26 2 0 0 0 0 16 31 1 0 0 0 0 17 23 1 1 0 0 0 17 30 1 0 0 0 0 18 23 1 1 0 0 0 18 31 1 0 0 0 0 19 24 1 1 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 6 0 0 0 21 24 1 1 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 6 1 6 0 0 0 24 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.23
Volume:	455.13
LogP:	2.591
LogD:	1.512
LogS:	-3.861
# Rotatable Bonds:	4
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.373
Synthetic Accessibility Score:	5.414
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	0.0001103311515180394
Pgp-inhibitor:	0.997
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.631
Plasma Protein Binding (PPB):	66.09783172607422%
Volume Distribution (VD):	1.342
Pgp-substrate:	32.08602523803711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	2.883
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.402
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.581
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.453
Maximum Recommended Daily Dose:	0.183
Skin Sensitization:	0.35
Carcinogencity:	0.02
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC69171

Natural Product ID:	NPC69171
*Common Name:**	AZSZOYDZIJLBMC-UOQWHXLTSA-N
IUPAC Name:	n.a.
Synonyms:	9-Deacetylstylatulide Lactone
Standard InCHIKey:	AZSZOYDZIJLBMC-UOQWHXLTSA-N
Standard InCHI:	InChI=1S/C24H34O8/c1-12-7-9-17(30-15(4)25)23(6)18(31-16(5)26)10-8-13(2)20(23)21(27)24(29)14(3)22(28)32-19(24)11-12/h8,11,14,17-21,27,29H,7,9-10H2,1-6H3/b12-11-/t14-,17+,18-,19-,20+,21+,23-,24-/m0/s1
SMILES:	CC(=O)O[C@@H]1CC/C(=C[C@H]2[C@@]([C@@H]([C@@H]3[C@]1(C)[C@H](CC=C3C)OC(=O)C)O)(O)[C@@H](C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463127
PubChem CID:	44584194
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

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.12	ug ml-1	PMID[567756]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[567756]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[567756]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.79	ug ml-1	PMID[567756]

☑ 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 NPC69171 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	207
0.1-0.2	1187
0.2-0.3	4229
0.3-0.4	8303
0.4-0.5	13826
0.5-0.6	6865
0.6-0.7	6042
0.7-0.8	1855
0.8-0.85	140
0.85-0.9	20
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474165
0.9895	High Similarity	NPC183571
0.95	High Similarity	NPC475922
0.9406	High Similarity	NPC161816
0.9406	High Similarity	NPC115257
0.9388	High Similarity	NPC4620
0.9307	High Similarity	NPC42662
0.9293	High Similarity	NPC475676
0.9293	High Similarity	NPC220964
0.9208	High Similarity	NPC94377
0.9109	High Similarity	NPC326994
0.9109	High Similarity	NPC324327
0.9109	High Similarity	NPC72813
0.9109	High Similarity	NPC194620
0.9109	High Similarity	NPC474421
0.9038	High Similarity	NPC473877
0.902	High Similarity	NPC233379
0.902	High Similarity	NPC14862
0.902	High Similarity	NPC169888
0.902	High Similarity	NPC474664
0.902	High Similarity	NPC327286
0.902	High Similarity	NPC55972
0.901	High Similarity	NPC9303
0.901	High Similarity	NPC16313
0.9	High Similarity	NPC19239
0.9	High Similarity	NPC474166
0.8932	High Similarity	NPC15218
0.8824	High Similarity	NPC475802
0.8785	High Similarity	NPC474333
0.8704	High Similarity	NPC296822
0.8692	High Similarity	NPC73314
0.8558	High Similarity	NPC475587
0.8558	High Similarity	NPC475510
0.8544	High Similarity	NPC296950
0.8544	High Similarity	NPC146731
0.8529	High Similarity	NPC474709
0.8476	Intermediate Similarity	NPC473939
0.8476	Intermediate Similarity	NPC473595
0.8476	Intermediate Similarity	NPC151393
0.8447	Intermediate Similarity	NPC475321
0.8416	Intermediate Similarity	NPC222303
0.8378	Intermediate Similarity	NPC470186
0.8367	Intermediate Similarity	NPC475972
0.8365	Intermediate Similarity	NPC258532
0.8364	Intermediate Similarity	NPC476712
0.8364	Intermediate Similarity	NPC476713
0.8333	Intermediate Similarity	NPC317687
0.8333	Intermediate Similarity	NPC269530
0.8318	Intermediate Similarity	NPC473594
0.8318	Intermediate Similarity	NPC474586
0.8318	Intermediate Similarity	NPC235014
0.8318	Intermediate Similarity	NPC473843
0.8318	Intermediate Similarity	NPC473975
0.8318	Intermediate Similarity	NPC281624
0.83	Intermediate Similarity	NPC36954
0.8283	Intermediate Similarity	NPC476300
0.8273	Intermediate Similarity	NPC476710
0.8273	Intermediate Similarity	NPC476711
0.8269	Intermediate Similarity	NPC159533
0.8269	Intermediate Similarity	NPC474775
0.8241	Intermediate Similarity	NPC317107
0.8241	Intermediate Similarity	NPC194619
0.8235	Intermediate Similarity	NPC471144
0.8229	Intermediate Similarity	NPC478112
0.8218	Intermediate Similarity	NPC54731
0.8218	Intermediate Similarity	NPC473859
0.8218	Intermediate Similarity	NPC230800
0.8218	Intermediate Similarity	NPC279621
0.8208	Intermediate Similarity	NPC187435
0.8208	Intermediate Similarity	NPC67321
0.8208	Intermediate Similarity	NPC112780
0.8198	Intermediate Similarity	NPC475323
0.8198	Intermediate Similarity	NPC473590
0.819	Intermediate Similarity	NPC472756
0.8182	Intermediate Similarity	NPC30515
0.8182	Intermediate Similarity	NPC184463
0.8173	Intermediate Similarity	NPC471148
0.8173	Intermediate Similarity	NPC149371
0.8173	Intermediate Similarity	NPC472754
0.8158	Intermediate Similarity	NPC282003
0.8158	Intermediate Similarity	NPC188222
0.8158	Intermediate Similarity	NPC310035
0.8155	Intermediate Similarity	NPC474718
0.8155	Intermediate Similarity	NPC288876
0.8148	Intermediate Similarity	NPC475134
0.8148	Intermediate Similarity	NPC475563
0.8148	Intermediate Similarity	NPC5103
0.8142	Intermediate Similarity	NPC475003
0.8137	Intermediate Similarity	NPC17326
0.8137	Intermediate Similarity	NPC134454
0.8131	Intermediate Similarity	NPC476479
0.8119	Intermediate Similarity	NPC37603
0.8119	Intermediate Similarity	NPC471786
0.8119	Intermediate Similarity	NPC471142
0.8119	Intermediate Similarity	NPC475659
0.8113	Intermediate Similarity	NPC127609
0.8113	Intermediate Similarity	NPC284365
0.8113	Intermediate Similarity	NPC123726
0.8108	Intermediate Similarity	NPC329869
0.81	Intermediate Similarity	NPC475912
0.8095	Intermediate Similarity	NPC8196
0.8095	Intermediate Similarity	NPC99266
0.8095	Intermediate Similarity	NPC472755
0.8091	Intermediate Similarity	NPC474410
0.8091	Intermediate Similarity	NPC469496
0.8091	Intermediate Similarity	NPC293658
0.8091	Intermediate Similarity	NPC477126
0.8091	Intermediate Similarity	NPC469454
0.8091	Intermediate Similarity	NPC469463
0.8087	Intermediate Similarity	NPC303006
0.8087	Intermediate Similarity	NPC67251
0.8081	Intermediate Similarity	NPC474232
0.8081	Intermediate Similarity	NPC51004
0.8077	Intermediate Similarity	NPC98225
0.8077	Intermediate Similarity	NPC308824
0.8077	Intermediate Similarity	NPC101067
0.8077	Intermediate Similarity	NPC47880
0.8077	Intermediate Similarity	NPC472753
0.8077	Intermediate Similarity	NPC164598
0.8077	Intermediate Similarity	NPC476134
0.8077	Intermediate Similarity	NPC474339
0.8073	Intermediate Similarity	NPC475480
0.8073	Intermediate Similarity	NPC324683
0.8073	Intermediate Similarity	NPC475668
0.8073	Intermediate Similarity	NPC473921
0.8061	Intermediate Similarity	NPC309656
0.8061	Intermediate Similarity	NPC476803
0.8058	Intermediate Similarity	NPC216478
0.8056	Intermediate Similarity	NPC472216
0.8056	Intermediate Similarity	NPC284828
0.8056	Intermediate Similarity	NPC173905
0.8056	Intermediate Similarity	NPC5475
0.8039	Intermediate Similarity	NPC21302
0.8039	Intermediate Similarity	NPC476315
0.8039	Intermediate Similarity	NPC11396
0.8037	Intermediate Similarity	NPC293512
0.8037	Intermediate Similarity	NPC477513
0.8037	Intermediate Similarity	NPC143609
0.8036	Intermediate Similarity	NPC176513
0.8036	Intermediate Similarity	NPC53396
0.8036	Intermediate Similarity	NPC470775
0.8036	Intermediate Similarity	NPC469684
0.8036	Intermediate Similarity	NPC473656
0.8036	Intermediate Similarity	NPC98249
0.802	Intermediate Similarity	NPC474247
0.802	Intermediate Similarity	NPC250075
0.8019	Intermediate Similarity	NPC203659
0.8019	Intermediate Similarity	NPC470104
0.8018	Intermediate Similarity	NPC117712
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC469606
0.8	Intermediate Similarity	NPC23786
0.8	Intermediate Similarity	NPC137430
0.8	Intermediate Similarity	NPC472552
0.8	Intermediate Similarity	NPC470265
0.8	Intermediate Similarity	NPC283567
0.8	Intermediate Similarity	NPC31058
0.8	Intermediate Similarity	NPC273005
0.7982	Intermediate Similarity	NPC472214
0.7982	Intermediate Similarity	NPC472215
0.7982	Intermediate Similarity	NPC119550
0.7981	Intermediate Similarity	NPC475949
0.7981	Intermediate Similarity	NPC272223
0.798	Intermediate Similarity	NPC473564
0.798	Intermediate Similarity	NPC307411
0.7965	Intermediate Similarity	NPC470776
0.7965	Intermediate Similarity	NPC284707
0.7963	Intermediate Similarity	NPC128795
0.7963	Intermediate Similarity	NPC217921
0.7963	Intermediate Similarity	NPC308191
0.7963	Intermediate Similarity	NPC322903
0.7963	Intermediate Similarity	NPC135015
0.7963	Intermediate Similarity	NPC48548
0.7963	Intermediate Similarity	NPC306265
0.7963	Intermediate Similarity	NPC472439
0.7963	Intermediate Similarity	NPC469916
0.7961	Intermediate Similarity	NPC474395
0.7961	Intermediate Similarity	NPC73911
0.7961	Intermediate Similarity	NPC124246
0.7961	Intermediate Similarity	NPC40812
0.7959	Intermediate Similarity	NPC476600
0.7946	Intermediate Similarity	NPC474734
0.7944	Intermediate Similarity	NPC111952
0.7944	Intermediate Similarity	NPC179891
0.7944	Intermediate Similarity	NPC472655
0.7941	Intermediate Similarity	NPC14961
0.7941	Intermediate Similarity	NPC270013
0.7941	Intermediate Similarity	NPC471141
0.7931	Intermediate Similarity	NPC91693
0.7931	Intermediate Similarity	NPC129992
0.7931	Intermediate Similarity	NPC265557
0.7931	Intermediate Similarity	NPC18945
0.7931	Intermediate Similarity	NPC105926
0.7928	Intermediate Similarity	NPC471204
0.7928	Intermediate Similarity	NPC264153
0.7928	Intermediate Similarity	NPC75167
0.7928	Intermediate Similarity	NPC311592
0.7925	Intermediate Similarity	NPC475945
0.7925	Intermediate Similarity	NPC110989
0.7925	Intermediate Similarity	NPC36688

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 NPC69171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	1729
0.2-0.3	3635
0.3-0.4	2326
0.4-0.5	762
0.5-0.6	340
0.6-0.7	151
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.79	Intermediate Similarity	NPD6698	Approved
0.79	Intermediate Similarity	NPD46	Approved
0.7885	Intermediate Similarity	NPD4225	Approved
0.787	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD6371	Approved
0.7798	Intermediate Similarity	NPD6686	Approved
0.7647	Intermediate Similarity	NPD7983	Approved
0.7565	Intermediate Similarity	NPD7115	Discovery
0.7458	Intermediate Similarity	NPD8513	Phase 3
0.7458	Intermediate Similarity	NPD8516	Approved
0.7458	Intermediate Similarity	NPD8517	Approved
0.7458	Intermediate Similarity	NPD8515	Approved
0.7434	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5779	Approved
0.7404	Intermediate Similarity	NPD5778	Approved
0.7345	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6399	Phase 3
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7638	Approved
0.7212	Intermediate Similarity	NPD7838	Discovery
0.7177	Intermediate Similarity	NPD7319	Approved
0.717	Intermediate Similarity	NPD5282	Discontinued
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7154	Intermediate Similarity	NPD8074	Phase 3
0.7143	Intermediate Similarity	NPD6411	Approved
0.7091	Intermediate Similarity	NPD5344	Discontinued
0.7083	Intermediate Similarity	NPD6319	Approved
0.708	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7507	Approved
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7048	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD8133	Approved
0.6981	Remote Similarity	NPD7637	Suspended
0.6975	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6101	Approved
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6412	Phase 2
0.6911	Remote Similarity	NPD8328	Phase 3
0.6909	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7492	Approved
0.6832	Remote Similarity	NPD5369	Approved
0.681	Remote Similarity	NPD6373	Approved
0.681	Remote Similarity	NPD6372	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6792	Remote Similarity	NPD1695	Approved
0.678	Remote Similarity	NPD8297	Approved
0.6777	Remote Similarity	NPD7328	Approved
0.6777	Remote Similarity	NPD7327	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD4269	Approved
0.6762	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD4250	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6727	Remote Similarity	NPD7839	Suspended
0.6723	Remote Similarity	NPD4632	Approved
0.6721	Remote Similarity	NPD7516	Approved
0.6699	Remote Similarity	NPD7154	Phase 3
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD6650	Approved
0.6695	Remote Similarity	NPD6649	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6635	Remote Similarity	NPD4786	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6613	Remote Similarity	NPD7503	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6602	Remote Similarity	NPD3667	Approved
0.6581	Remote Similarity	NPD7320	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6581	Remote Similarity	NPD6899	Approved
0.6579	Remote Similarity	NPD7632	Discontinued
0.6571	Remote Similarity	NPD5363	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6571	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4821	Approved
0.6569	Remote Similarity	NPD4252	Approved
0.6569	Remote Similarity	NPD4822	Approved
0.6569	Remote Similarity	NPD4819	Approved
0.6569	Remote Similarity	NPD4820	Approved
0.6566	Remote Similarity	NPD8039	Approved
0.656	Remote Similarity	NPD5988	Approved
0.6545	Remote Similarity	NPD7748	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6538	Remote Similarity	NPD5362	Discontinued
0.6535	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8273	Phase 1
0.6535	Remote Similarity	NPD8451	Approved
0.6514	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD6882	Approved
0.6496	Remote Similarity	NPD5701	Approved
0.6496	Remote Similarity	NPD5697	Approved
0.6486	Remote Similarity	NPD5695	Phase 3
0.6484	Remote Similarity	NPD8448	Approved
0.6476	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.646	Remote Similarity	NPD5696	Approved
0.6442	Remote Similarity	NPD6435	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6418	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8130	Phase 1
0.6417	Remote Similarity	NPD6617	Approved
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD7900	Approved
0.6396	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6013	Approved
0.6387	Remote Similarity	NPD6012	Approved
0.6387	Remote Similarity	NPD6014	Approved
0.6381	Remote Similarity	NPD6695	Phase 3
0.6378	Remote Similarity	NPD7642	Approved
0.6378	Remote Similarity	NPD7604	Phase 2
0.6373	Remote Similarity	NPD4268	Approved
0.6373	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6845	Suspended
0.6355	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD6409	Approved
0.6355	Remote Similarity	NPD3618	Phase 1
0.6355	Remote Similarity	NPD5330	Approved
0.6355	Remote Similarity	NPD7146	Approved
0.6355	Remote Similarity	NPD6684	Approved
0.6355	Remote Similarity	NPD7521	Approved
0.6349	Remote Similarity	NPD8444	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6336	Remote Similarity	NPD8392	Approved
0.6336	Remote Similarity	NPD8391	Approved
0.6336	Remote Similarity	NPD8390	Approved
0.633	Remote Similarity	NPD6051	Approved
0.6328	Remote Similarity	NPD8299	Approved
0.6328	Remote Similarity	NPD8342	Approved
0.6328	Remote Similarity	NPD8341	Approved
0.6328	Remote Similarity	NPD8340	Approved
0.6308	Remote Similarity	NPD6033	Approved
0.6303	Remote Similarity	NPD6011	Approved
0.6281	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD5368	Approved
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD6672	Approved
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5737	Approved
0.6228	Remote Similarity	NPD4755	Approved
0.6226	Remote Similarity	NPD6110	Phase 1
0.6216	Remote Similarity	NPD5284	Approved
0.6216	Remote Similarity	NPD5281	Approved
0.6216	Remote Similarity	NPD5693	Phase 1
0.6198	Remote Similarity	NPD6421	Discontinued
0.6195	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4753	Phase 2
0.6182	Remote Similarity	NPD5328	Approved
0.6168	Remote Similarity	NPD3668	Phase 3
0.6168	Remote Similarity	NPD3133	Approved
0.6168	Remote Similarity	NPD3665	Phase 1
0.6168	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD4202	Approved
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5211	Phase 2
0.6148	Remote Similarity	NPD2204	Approved
0.6147	Remote Similarity	NPD7750	Discontinued
0.6132	Remote Similarity	NPD5209	Approved
0.6124	Remote Similarity	NPD6067	Discontinued
0.6121	Remote Similarity	NPD4696	Approved
0.6121	Remote Similarity	NPD5285	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