NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	2.336
LogD:	1.577
LogS:	-2.358
# Rotatable Bonds:	2
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.018
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.051
MDCK Permeability:	1.8057182387565263e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	89.40811920166016%
Volume Distribution (VD):	0.283
Pgp-substrate:	12.805896759033203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.405
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	7.257
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.738
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.852
Maximum Recommended Daily Dose:	0.592
Skin Sensitization:	0.838
Carcinogencity:	0.827
Eye Corrosion:	0.778
Eye Irritation:	0.919
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC18543

Natural Product ID:	NPC18543
*Common Name:**	Damcinic Acid
IUPAC Name:	2-[(3aS,5R,8S,8aS)-3a,8-dimethyl-3-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	CRXWIWHBLVNJSP-LIBKGXAOSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-4-5-11(10(2)14(17)18)8-15(3)12(9)6-7-13(15)16/h9,11-12H,2,4-8H2,1,3H3,(H,17,18)/t9-,11+,12-,15-/m0/s1
SMILES:	C[C@H]1CC[C@H](C[C@]2([C@H]1CCC2=O)C)C(=C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2286470
PubChem CID:	11747064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002873] Pseudoguaianes

*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
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31009220]
NPO15781	Ambrosia ambrosioids	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15781	Ambrosia ambrosioids	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15781	Ambrosia ambrosioids	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	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	2
Others	15

Activity Type	# Activity
Organism	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	1090000.0	nM	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	70.5	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	44.6	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	29.5	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	6.3	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	3.6	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	600000.0	nM	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	79.2	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	64.6	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	50.0	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	31.3	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	4.2	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	28.3	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	38.3	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	40.0	%	PMID[556367]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	41.7	%	PMID[556367]

☑ 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 NPC18543 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	178
0.1-0.2	1878
0.2-0.3	11171
0.3-0.4	14434
0.4-0.5	7691
0.5-0.6	5577
0.6-0.7	1600
0.7-0.8	161
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8714	High Similarity	NPC29328
0.8551	High Similarity	NPC476629
0.8378	Intermediate Similarity	NPC472014
0.8158	Intermediate Similarity	NPC476624
0.8158	Intermediate Similarity	NPC472013
0.8143	Intermediate Similarity	NPC476626
0.8056	Intermediate Similarity	NPC235586
0.8052	Intermediate Similarity	NPC476625
0.7975	Intermediate Similarity	NPC65350
0.7975	Intermediate Similarity	NPC472740
0.7917	Intermediate Similarity	NPC67608
0.7895	Intermediate Similarity	NPC97377
0.7895	Intermediate Similarity	NPC471035
0.7895	Intermediate Similarity	NPC212661
0.7895	Intermediate Similarity	NPC74685
0.7867	Intermediate Similarity	NPC39362
0.7821	Intermediate Similarity	NPC6823
0.7821	Intermediate Similarity	NPC290508
0.7821	Intermediate Similarity	NPC73052
0.7821	Intermediate Similarity	NPC293418
0.7805	Intermediate Similarity	NPC201658
0.7792	Intermediate Similarity	NPC476627
0.7763	Intermediate Similarity	NPC20466
0.7733	Intermediate Similarity	NPC7382
0.7714	Intermediate Similarity	NPC53642
0.7714	Intermediate Similarity	NPC470325
0.7703	Intermediate Similarity	NPC288667
0.7692	Intermediate Similarity	NPC7232
0.7683	Intermediate Similarity	NPC56593
0.7639	Intermediate Similarity	NPC263161
0.7632	Intermediate Similarity	NPC476795
0.7632	Intermediate Similarity	NPC201263
0.7619	Intermediate Similarity	NPC12872
0.7619	Intermediate Similarity	NPC168679
0.76	Intermediate Similarity	NPC472813
0.7595	Intermediate Similarity	NPC45495
0.7564	Intermediate Similarity	NPC169095
0.7561	Intermediate Similarity	NPC476628
0.7561	Intermediate Similarity	NPC142649
0.7534	Intermediate Similarity	NPC476614
0.7532	Intermediate Similarity	NPC215481
0.7532	Intermediate Similarity	NPC182848
0.7532	Intermediate Similarity	NPC469646
0.7531	Intermediate Similarity	NPC54468
0.7531	Intermediate Similarity	NPC97913
0.7531	Intermediate Similarity	NPC245665
0.75	Intermediate Similarity	NPC126248
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC143979
0.75	Intermediate Similarity	NPC46610
0.75	Intermediate Similarity	NPC320537
0.75	Intermediate Similarity	NPC18819
0.75	Intermediate Similarity	NPC206875
0.747	Intermediate Similarity	NPC236692
0.747	Intermediate Similarity	NPC309757
0.7468	Intermediate Similarity	NPC477371
0.7468	Intermediate Similarity	NPC192744
0.7468	Intermediate Similarity	NPC229204
0.7467	Intermediate Similarity	NPC469737
0.7439	Intermediate Similarity	NPC224386
0.7439	Intermediate Similarity	NPC164577
0.7439	Intermediate Similarity	NPC194859
0.7436	Intermediate Similarity	NPC66105
0.7436	Intermediate Similarity	NPC208223
0.7432	Intermediate Similarity	NPC5714
0.7412	Intermediate Similarity	NPC262043
0.7412	Intermediate Similarity	NPC155935
0.7403	Intermediate Similarity	NPC77501
0.7403	Intermediate Similarity	NPC251435
0.7403	Intermediate Similarity	NPC472327
0.7397	Intermediate Similarity	NPC60120
0.7381	Intermediate Similarity	NPC136948
0.7381	Intermediate Similarity	NPC118601
0.7375	Intermediate Similarity	NPC51507
0.7368	Intermediate Similarity	NPC244708
0.7368	Intermediate Similarity	NPC161187
0.7368	Intermediate Similarity	NPC330659
0.7368	Intermediate Similarity	NPC35656
0.7356	Intermediate Similarity	NPC473234
0.7356	Intermediate Similarity	NPC60386
0.7356	Intermediate Similarity	NPC200237
0.7356	Intermediate Similarity	NPC473273
0.7356	Intermediate Similarity	NPC153590
0.7356	Intermediate Similarity	NPC473263
0.7356	Intermediate Similarity	NPC308656
0.7349	Intermediate Similarity	NPC300082
0.7349	Intermediate Similarity	NPC284534
0.7349	Intermediate Similarity	NPC29447
0.7349	Intermediate Similarity	NPC204105
0.7342	Intermediate Similarity	NPC74410
0.7342	Intermediate Similarity	NPC198240
0.7342	Intermediate Similarity	NPC321690
0.7326	Intermediate Similarity	NPC54065
0.7326	Intermediate Similarity	NPC35809
0.7326	Intermediate Similarity	NPC297474
0.7317	Intermediate Similarity	NPC49019
0.7317	Intermediate Similarity	NPC128246
0.7317	Intermediate Similarity	NPC310470
0.7308	Intermediate Similarity	NPC279537
0.7308	Intermediate Similarity	NPC246445
0.7297	Intermediate Similarity	NPC36616
0.7297	Intermediate Similarity	NPC290445
0.7294	Intermediate Similarity	NPC217983
0.7294	Intermediate Similarity	NPC207114
0.7294	Intermediate Similarity	NPC117122
0.7294	Intermediate Similarity	NPC178875
0.7286	Intermediate Similarity	NPC40206
0.7286	Intermediate Similarity	NPC472328
0.7284	Intermediate Similarity	NPC136150
0.7284	Intermediate Similarity	NPC147066
0.7284	Intermediate Similarity	NPC201912
0.7284	Intermediate Similarity	NPC38350
0.7273	Intermediate Similarity	NPC213223
0.7273	Intermediate Similarity	NPC473331
0.7262	Intermediate Similarity	NPC187661
0.7262	Intermediate Similarity	NPC472869
0.7262	Intermediate Similarity	NPC6247
0.7262	Intermediate Similarity	NPC70661
0.7262	Intermediate Similarity	NPC238593
0.7262	Intermediate Similarity	NPC186975
0.726	Intermediate Similarity	NPC103734
0.725	Intermediate Similarity	NPC181195
0.725	Intermediate Similarity	NPC261125
0.725	Intermediate Similarity	NPC263951
0.7241	Intermediate Similarity	NPC35959
0.7241	Intermediate Similarity	NPC474018
0.7241	Intermediate Similarity	NPC171360
0.7241	Intermediate Similarity	NPC63193
0.7241	Intermediate Similarity	NPC293001
0.7241	Intermediate Similarity	NPC133888
0.7241	Intermediate Similarity	NPC29821
0.7241	Intermediate Similarity	NPC57304
0.7241	Intermediate Similarity	NPC473986
0.7241	Intermediate Similarity	NPC204341
0.7229	Intermediate Similarity	NPC472865
0.7229	Intermediate Similarity	NPC19849
0.7229	Intermediate Similarity	NPC156485
0.7229	Intermediate Similarity	NPC165064
0.7229	Intermediate Similarity	NPC248758
0.7229	Intermediate Similarity	NPC472864
0.7215	Intermediate Similarity	NPC165711
0.7215	Intermediate Similarity	NPC137547
0.7215	Intermediate Similarity	NPC106078
0.7215	Intermediate Similarity	NPC68828
0.7215	Intermediate Similarity	NPC475932
0.7215	Intermediate Similarity	NPC61952
0.7209	Intermediate Similarity	NPC477215
0.7209	Intermediate Similarity	NPC476388
0.7209	Intermediate Similarity	NPC170775
0.7209	Intermediate Similarity	NPC214387
0.7209	Intermediate Similarity	NPC232747
0.72	Intermediate Similarity	NPC475952
0.7195	Intermediate Similarity	NPC170985
0.7195	Intermediate Similarity	NPC260956
0.7195	Intermediate Similarity	NPC320514
0.7195	Intermediate Similarity	NPC20262
0.7195	Intermediate Similarity	NPC256750
0.7195	Intermediate Similarity	NPC133391
0.7179	Intermediate Similarity	NPC474011
0.7179	Intermediate Similarity	NPC89374
0.7176	Intermediate Similarity	NPC236618
0.7162	Intermediate Similarity	NPC469868
0.716	Intermediate Similarity	NPC258965
0.716	Intermediate Similarity	NPC69271
0.716	Intermediate Similarity	NPC164218
0.716	Intermediate Similarity	NPC74673
0.716	Intermediate Similarity	NPC156658
0.7143	Intermediate Similarity	NPC300940
0.7143	Intermediate Similarity	NPC245434
0.7143	Intermediate Similarity	NPC269638
0.7126	Intermediate Similarity	NPC472866
0.7126	Intermediate Similarity	NPC477149
0.7126	Intermediate Similarity	NPC19087
0.7126	Intermediate Similarity	NPC477147
0.7125	Intermediate Similarity	NPC62336
0.7125	Intermediate Similarity	NPC269543
0.7125	Intermediate Similarity	NPC179028
0.7125	Intermediate Similarity	NPC476810
0.7125	Intermediate Similarity	NPC247783
0.7125	Intermediate Similarity	NPC192006
0.7111	Intermediate Similarity	NPC91771
0.7111	Intermediate Similarity	NPC142529
0.7108	Intermediate Similarity	NPC168188
0.7108	Intermediate Similarity	NPC83569
0.7108	Intermediate Similarity	NPC243347
0.7108	Intermediate Similarity	NPC107253
0.7108	Intermediate Similarity	NPC470015
0.7108	Intermediate Similarity	NPC477373
0.7108	Intermediate Similarity	NPC69279
0.7108	Intermediate Similarity	NPC215294
0.7105	Intermediate Similarity	NPC91369
0.7105	Intermediate Similarity	NPC280256
0.7093	Intermediate Similarity	NPC472870
0.7093	Intermediate Similarity	NPC79549
0.7089	Intermediate Similarity	NPC180886
0.7089	Intermediate Similarity	NPC263582
0.7079	Intermediate Similarity	NPC167219
0.7073	Intermediate Similarity	NPC232625
0.7073	Intermediate Similarity	NPC103754
0.7073	Intermediate Similarity	NPC470241

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 NPC18543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	2753
0.2-0.3	4036
0.3-0.4	1473
0.4-0.5	359
0.5-0.6	256
0.6-0.7	60
0.7-0.8	2
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
0.7342	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5363	Approved
0.6932	Remote Similarity	NPD5785	Approved
0.6905	Remote Similarity	NPD4788	Approved
0.6813	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4223	Phase 3
0.6786	Remote Similarity	NPD4270	Approved
0.6786	Remote Similarity	NPD4269	Approved
0.6786	Remote Similarity	NPD4221	Approved
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3617	Approved
0.6706	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6628	Remote Similarity	NPD4197	Approved
0.6628	Remote Similarity	NPD3665	Phase 1
0.6628	Remote Similarity	NPD3666	Approved
0.6628	Remote Similarity	NPD3133	Approved
0.6588	Remote Similarity	NPD3667	Approved
0.6579	Remote Similarity	NPD4224	Phase 2
0.6552	Remote Similarity	NPD5329	Approved
0.6548	Remote Similarity	NPD4252	Approved
0.6548	Remote Similarity	NPD5368	Approved
0.6548	Remote Similarity	NPD4695	Discontinued
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5280	Approved
0.6477	Remote Similarity	NPD5786	Approved
0.6477	Remote Similarity	NPD4688	Approved
0.6477	Remote Similarity	NPD4138	Approved
0.6477	Remote Similarity	NPD4623	Approved
0.6477	Remote Similarity	NPD5279	Phase 3
0.6477	Remote Similarity	NPD7146	Approved
0.6477	Remote Similarity	NPD4689	Approved
0.6477	Remote Similarity	NPD4690	Approved
0.6477	Remote Similarity	NPD7521	Approved
0.6477	Remote Similarity	NPD5205	Approved
0.6477	Remote Similarity	NPD5330	Approved
0.6477	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD4694	Approved
0.6477	Remote Similarity	NPD4693	Phase 3
0.6477	Remote Similarity	NPD4519	Discontinued
0.6477	Remote Similarity	NPD7334	Approved
0.6477	Remote Similarity	NPD3618	Phase 1
0.6477	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD857	Phase 3
0.6462	Remote Similarity	NPD634	Phase 3
0.6452	Remote Similarity	NPD5695	Phase 3
0.6447	Remote Similarity	NPD7341	Phase 2
0.6438	Remote Similarity	NPD3198	Approved
0.6437	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6399	Phase 3
0.6395	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6435	Approved
0.6375	Remote Similarity	NPD6081	Approved
0.6364	Remote Similarity	NPD7331	Phase 2
0.6364	Remote Similarity	NPD1694	Approved
0.6354	Remote Similarity	NPD6404	Discontinued
0.6353	Remote Similarity	NPD4820	Approved
0.6353	Remote Similarity	NPD4822	Approved
0.6353	Remote Similarity	NPD4819	Approved
0.6353	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD4518	Approved
0.6333	Remote Similarity	NPD6903	Approved
0.6333	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5208	Approved
0.6333	Remote Similarity	NPD5737	Approved
0.6333	Remote Similarity	NPD6672	Approved
0.6322	Remote Similarity	NPD5332	Approved
0.6322	Remote Similarity	NPD7154	Phase 3
0.6322	Remote Similarity	NPD5331	Approved
0.6316	Remote Similarity	NPD6084	Phase 2
0.6316	Remote Similarity	NPD6083	Phase 2
0.631	Remote Similarity	NPD4271	Approved
0.631	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD8035	Phase 2
0.6304	Remote Similarity	NPD8034	Phase 2
0.6304	Remote Similarity	NPD6079	Approved
0.6292	Remote Similarity	NPD6098	Approved
0.6279	Remote Similarity	NPD4139	Approved
0.6279	Remote Similarity	NPD4790	Discontinued
0.6279	Remote Similarity	NPD4692	Approved
0.6269	Remote Similarity	NPD622	Approved
0.6264	Remote Similarity	NPD4753	Phase 2
0.6264	Remote Similarity	NPD1695	Approved
0.6264	Remote Similarity	NPD6080	Approved
0.6264	Remote Similarity	NPD6904	Approved
0.6264	Remote Similarity	NPD5328	Approved
0.6264	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD4691	Approved
0.6235	Remote Similarity	NPD4195	Approved
0.6234	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD9298	Approved
0.6196	Remote Similarity	NPD5692	Phase 3
0.6196	Remote Similarity	NPD4096	Approved
0.6196	Remote Similarity	NPD5207	Approved
0.6163	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD375	Phase 2
0.6129	Remote Similarity	NPD7515	Phase 2
0.6129	Remote Similarity	NPD5694	Approved
0.6129	Remote Similarity	NPD6050	Approved
0.6125	Remote Similarity	NPD4137	Phase 3
0.6117	Remote Similarity	NPD6371	Approved
0.6105	Remote Similarity	NPD4629	Approved
0.6105	Remote Similarity	NPD5210	Approved
0.6087	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3668	Phase 3
0.6064	Remote Similarity	NPD4202	Approved
0.6061	Remote Similarity	NPD5211	Phase 2
0.6056	Remote Similarity	NPD3172	Approved
0.6049	Remote Similarity	NPD4747	Approved
0.6044	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD5221	Approved
0.6042	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5222	Approved
0.6024	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD4058	Approved
0.602	Remote Similarity	NPD7639	Approved
0.602	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD4756	Discovery
0.6	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5360	Phase 3
0.6	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD5697	Approved
0.5979	Remote Similarity	NPD5173	Approved
0.5976	Remote Similarity	NPD5276	Approved
0.5972	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD3195	Phase 2
0.5972	Remote Similarity	NPD4266	Approved
0.5972	Remote Similarity	NPD3196	Approved
0.5972	Remote Similarity	NPD3194	Approved
0.5952	Remote Similarity	NPD3702	Approved
0.5941	Remote Similarity	NPD5141	Approved
0.5938	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3698	Phase 2
0.5926	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD6881	Approved
0.5922	Remote Similarity	NPD6899	Approved
0.5918	Remote Similarity	NPD7638	Approved
0.5915	Remote Similarity	NPD3186	Phase 1
0.5895	Remote Similarity	NPD5133	Approved
0.5882	Remote Similarity	NPD6117	Approved
0.5882	Remote Similarity	NPD7128	Approved
0.5882	Remote Similarity	NPD5739	Approved
0.5882	Remote Similarity	NPD6402	Approved
0.5882	Remote Similarity	NPD6675	Approved
0.5876	Remote Similarity	NPD7614	Phase 1
0.5876	Remote Similarity	NPD4697	Phase 3
0.5865	Remote Similarity	NPD6012	Approved
0.5865	Remote Similarity	NPD6013	Approved
0.5865	Remote Similarity	NPD6014	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD5285	Approved
0.5854	Remote Similarity	NPD4245	Approved
0.5854	Remote Similarity	NPD4789	Approved
0.5854	Remote Similarity	NPD4244	Approved
0.5843	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD5733	Approved
0.5833	Remote Similarity	NPD4687	Approved
0.5825	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5701	Approved
0.5824	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD1696	Phase 3
0.5816	Remote Similarity	NPD7902	Approved
0.5816	Remote Similarity	NPD4755	Approved
0.5814	Remote Similarity	NPD6116	Phase 1
0.581	Remote Similarity	NPD7102	Approved
0.581	Remote Similarity	NPD6883	Approved
0.581	Remote Similarity	NPD7290	Approved
0.5802	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5223	Approved
0.5789	Remote Similarity	NPD6411	Approved
0.5789	Remote Similarity	NPD7637	Suspended
0.5783	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4758	Discontinued
0.5783	Remote Similarity	NPD5777	Approved
0.578	Remote Similarity	NPD7115	Discovery
0.5773	Remote Similarity	NPD5654	Approved
0.5769	Remote Similarity	NPD7320	Approved
0.5769	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD8039	Approved
0.5761	Remote Similarity	NPD4249	Approved
0.5758	Remote Similarity	NPD4225	Approved
0.5755	Remote Similarity	NPD6847	Approved
0.5755	Remote Similarity	NPD8130	Phase 1
0.5755	Remote Similarity	NPD6650	Approved
0.5755	Remote Similarity	NPD6869	Approved
0.5755	Remote Similarity	NPD6617	Approved
0.5755	Remote Similarity	NPD6649	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