NPASS Compound

Structure

CID268039 OpenBabel06191716072D 21 22 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 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 2.5981 3.5000 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 1.7321 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 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 -1.7321 -1.0000 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 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 1 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 16 17 1 0 0 0 0 17 20 1 1 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	3.592
LogD:	4.001
LogS:	-4.535
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.548
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.646
MDCK Permeability:	2.1988083972246386e-05
Pgp-inhibitor:	0.161
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.218
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	65.66553497314453%
Volume Distribution (VD):	2.362
Pgp-substrate:	22.836084365844727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.752
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.548
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	6.848
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.186
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.954
Carcinogencity:	0.378
Eye Corrosion:	0.954
Eye Irritation:	0.94
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC268039

Natural Product ID:	NPC268039
*Common Name:**	Trans-Communal
IUPAC Name:	(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carbaldehyde
Synonyms:
Standard InCHIKey:	GBIAINFWNNBJAS-OCHVYMGISA-N
Standard InCHI:	InChI=1S/C20H30O/c1-6-15(2)8-10-17-16(3)9-11-18-19(4,14-21)12-7-13-20(17,18)5/h6,8,14,17-18H,1,3,7,9-13H2,2,4-5H3/b15-8+/t17-,18-,19+,20+/m0/s1
SMILES:	C=C/C(=C/C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C=O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385638
PubChem CID:	73351971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[475840]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[475840]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[475840]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[475840]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[475840]

☑ 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 NPC268039 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	227
0.1-0.2	1667
0.2-0.3	10864
0.3-0.4	15943
0.4-0.5	8388
0.5-0.6	4264
0.6-0.7	1193
0.7-0.8	135
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC193770
0.8571	High Similarity	NPC469793
0.8571	High Similarity	NPC469796
0.8438	Intermediate Similarity	NPC202118
0.8438	Intermediate Similarity	NPC197238
0.8358	Intermediate Similarity	NPC155198
0.8308	Intermediate Similarity	NPC52449
0.8308	Intermediate Similarity	NPC469662
0.8308	Intermediate Similarity	NPC169275
0.8209	Intermediate Similarity	NPC290350
0.8209	Intermediate Similarity	NPC4370
0.8028	Intermediate Similarity	NPC128346
0.8028	Intermediate Similarity	NPC211641
0.8028	Intermediate Similarity	NPC219232
0.8	Intermediate Similarity	NPC470078
0.7846	Intermediate Similarity	NPC127582
0.7826	Intermediate Similarity	NPC310992
0.7794	Intermediate Similarity	NPC323005
0.7778	Intermediate Similarity	NPC474797
0.7778	Intermediate Similarity	NPC474796
0.7778	Intermediate Similarity	NPC237591
0.7778	Intermediate Similarity	NPC329866
0.7778	Intermediate Similarity	NPC3753
0.7746	Intermediate Similarity	NPC474562
0.7733	Intermediate Similarity	NPC170793
0.7727	Intermediate Similarity	NPC60565
0.7714	Intermediate Similarity	NPC182815
0.7705	Intermediate Similarity	NPC22182
0.7671	Intermediate Similarity	NPC473171
0.7671	Intermediate Similarity	NPC476844
0.7656	Intermediate Similarity	NPC22019
0.7656	Intermediate Similarity	NPC281986
0.7656	Intermediate Similarity	NPC208749
0.7656	Intermediate Similarity	NPC321568
0.7632	Intermediate Similarity	NPC474509
0.7619	Intermediate Similarity	NPC188789
0.7619	Intermediate Similarity	NPC200258
0.76	Intermediate Similarity	NPC59436
0.76	Intermediate Similarity	NPC115515
0.7571	Intermediate Similarity	NPC39157
0.7571	Intermediate Similarity	NPC260474
0.7571	Intermediate Similarity	NPC82477
0.7571	Intermediate Similarity	NPC188292
0.7571	Intermediate Similarity	NPC296697
0.7571	Intermediate Similarity	NPC20610
0.7571	Intermediate Similarity	NPC142754
0.7568	Intermediate Similarity	NPC19907
0.7538	Intermediate Similarity	NPC60772
0.7534	Intermediate Similarity	NPC166797
0.75	Intermediate Similarity	NPC115023
0.75	Intermediate Similarity	NPC54123
0.75	Intermediate Similarity	NPC474113
0.75	Intermediate Similarity	NPC285371
0.75	Intermediate Similarity	NPC475124
0.7465	Intermediate Similarity	NPC286814
0.7465	Intermediate Similarity	NPC139397
0.746	Intermediate Similarity	NPC250539
0.7436	Intermediate Similarity	NPC94200
0.7429	Intermediate Similarity	NPC20181
0.7429	Intermediate Similarity	NPC220210
0.7424	Intermediate Similarity	NPC472304
0.7424	Intermediate Similarity	NPC276764
0.7397	Intermediate Similarity	NPC144947
0.7397	Intermediate Similarity	NPC251705
0.7391	Intermediate Similarity	NPC251118
0.7385	Intermediate Similarity	NPC115385
0.7375	Intermediate Similarity	NPC33881
0.7368	Intermediate Similarity	NPC82635
0.7368	Intermediate Similarity	NPC4827
0.7361	Intermediate Similarity	NPC265782
0.7361	Intermediate Similarity	NPC260040
0.7361	Intermediate Similarity	NPC40574
0.7361	Intermediate Similarity	NPC214770
0.7361	Intermediate Similarity	NPC307176
0.7361	Intermediate Similarity	NPC251929
0.7361	Intermediate Similarity	NPC477856
0.7361	Intermediate Similarity	NPC282593
0.7361	Intermediate Similarity	NPC2634
0.7361	Intermediate Similarity	NPC159577
0.7361	Intermediate Similarity	NPC35734
0.7353	Intermediate Similarity	NPC288253
0.7342	Intermediate Similarity	NPC312480
0.7333	Intermediate Similarity	NPC899
0.7324	Intermediate Similarity	NPC87141
0.7308	Intermediate Similarity	NPC474955
0.7308	Intermediate Similarity	NPC121984
0.7308	Intermediate Similarity	NPC90055
0.7297	Intermediate Similarity	NPC283908
0.7297	Intermediate Similarity	NPC476046
0.7297	Intermediate Similarity	NPC161923
0.7297	Intermediate Similarity	NPC241854
0.7297	Intermediate Similarity	NPC238146
0.7297	Intermediate Similarity	NPC306928
0.7297	Intermediate Similarity	NPC103958
0.7297	Intermediate Similarity	NPC309852
0.7297	Intermediate Similarity	NPC183503
0.7297	Intermediate Similarity	NPC168975
0.7297	Intermediate Similarity	NPC251970
0.7297	Intermediate Similarity	NPC75485
0.7297	Intermediate Similarity	NPC20025
0.7286	Intermediate Similarity	NPC149680
0.7284	Intermediate Similarity	NPC168248
0.7273	Intermediate Similarity	NPC56905
0.7273	Intermediate Similarity	NPC90965
0.7273	Intermediate Similarity	NPC27610
0.726	Intermediate Similarity	NPC133253
0.726	Intermediate Similarity	NPC181204
0.726	Intermediate Similarity	NPC72343
0.726	Intermediate Similarity	NPC234707
0.726	Intermediate Similarity	NPC304983
0.726	Intermediate Similarity	NPC190035
0.726	Intermediate Similarity	NPC225467
0.7258	Intermediate Similarity	NPC236623
0.725	Intermediate Similarity	NPC139566
0.7246	Intermediate Similarity	NPC4638
0.7222	Intermediate Similarity	NPC256846
0.7215	Intermediate Similarity	NPC142683
0.7215	Intermediate Similarity	NPC268122
0.7206	Intermediate Similarity	NPC213152
0.72	Intermediate Similarity	NPC279666
0.72	Intermediate Similarity	NPC192540
0.72	Intermediate Similarity	NPC293803
0.7188	Intermediate Similarity	NPC95581
0.7167	Intermediate Similarity	NPC195246
0.7167	Intermediate Similarity	NPC276009
0.7167	Intermediate Similarity	NPC22098
0.7162	Intermediate Similarity	NPC303613
0.7162	Intermediate Similarity	NPC470044
0.7162	Intermediate Similarity	NPC470045
0.7162	Intermediate Similarity	NPC474488
0.7162	Intermediate Similarity	NPC474228
0.7143	Intermediate Similarity	NPC470052
0.7143	Intermediate Similarity	NPC228911
0.7143	Intermediate Similarity	NPC239098
0.7125	Intermediate Similarity	NPC118423
0.7125	Intermediate Similarity	NPC474976
0.7125	Intermediate Similarity	NPC307258
0.7125	Intermediate Similarity	NPC474790
0.7121	Intermediate Similarity	NPC267626
0.7121	Intermediate Similarity	NPC55004
0.7121	Intermediate Similarity	NPC230823
0.7121	Intermediate Similarity	NPC49575
0.7105	Intermediate Similarity	NPC4509
0.7105	Intermediate Similarity	NPC309399
0.7105	Intermediate Similarity	NPC69143
0.7105	Intermediate Similarity	NPC69408
0.7089	Intermediate Similarity	NPC14151
0.7089	Intermediate Similarity	NPC4166
0.7067	Intermediate Similarity	NPC159497
0.7067	Intermediate Similarity	NPC301065
0.7059	Intermediate Similarity	NPC125226
0.7051	Intermediate Similarity	NPC152061
0.7051	Intermediate Similarity	NPC476177
0.7027	Intermediate Similarity	NPC21944
0.7027	Intermediate Similarity	NPC305501
0.7027	Intermediate Similarity	NPC160817
0.7015	Intermediate Similarity	NPC266295
0.7015	Intermediate Similarity	NPC311852
0.7015	Intermediate Similarity	NPC94991
0.7015	Intermediate Similarity	NPC30215
0.7013	Intermediate Similarity	NPC470557
0.7013	Intermediate Similarity	NPC325946
0.7013	Intermediate Similarity	NPC91665
0.7013	Intermediate Similarity	NPC472300
0.7	Intermediate Similarity	NPC469805
0.7	Intermediate Similarity	NPC469799
0.7	Intermediate Similarity	NPC469806
0.7	Intermediate Similarity	NPC6697
0.7	Intermediate Similarity	NPC239754
0.7	Intermediate Similarity	NPC311092
0.7	Intermediate Similarity	NPC469804
0.7	Intermediate Similarity	NPC212210
0.7	Intermediate Similarity	NPC470813
0.6988	Remote Similarity	NPC141292
0.6984	Remote Similarity	NPC30433
0.6974	Remote Similarity	NPC255650
0.6974	Remote Similarity	NPC65650
0.6974	Remote Similarity	NPC476346
0.6962	Remote Similarity	NPC469798
0.6962	Remote Similarity	NPC472478
0.6962	Remote Similarity	NPC469797
0.6962	Remote Similarity	NPC2482
0.6957	Remote Similarity	NPC469728
0.6951	Remote Similarity	NPC2709
0.6951	Remote Similarity	NPC76333
0.6935	Remote Similarity	NPC22765
0.6933	Remote Similarity	NPC56747
0.6933	Remote Similarity	NPC180015
0.6933	Remote Similarity	NPC109576
0.6933	Remote Similarity	NPC130016
0.6923	Remote Similarity	NPC247783
0.6923	Remote Similarity	NPC100809
0.6923	Remote Similarity	NPC189485
0.6923	Remote Similarity	NPC269543
0.6923	Remote Similarity	NPC209431
0.6914	Remote Similarity	NPC3856
0.6914	Remote Similarity	NPC279639
0.6912	Remote Similarity	NPC259261
0.6905	Remote Similarity	NPC310752
0.6905	Remote Similarity	NPC472220

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 NPC268039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1779
0.2-0.3	4445
0.3-0.4	1950
0.4-0.5	478
0.5-0.6	205
0.6-0.7	66
0.7-0.8	7
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	NPD4058	Approved
0.7571	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD4687	Approved
0.75	Intermediate Similarity	NPD5276	Approved
0.7465	Intermediate Similarity	NPD4137	Phase 3
0.7361	Intermediate Similarity	NPD4747	Approved
0.7361	Intermediate Similarity	NPD4691	Approved
0.7297	Intermediate Similarity	NPD5733	Approved
0.679	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3667	Approved
0.6765	Remote Similarity	NPD287	Approved
0.6753	Remote Similarity	NPD8039	Approved
0.6716	Remote Similarity	NPD4219	Approved
0.6707	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6627	Remote Similarity	NPD3665	Phase 1
0.6627	Remote Similarity	NPD4786	Approved
0.6627	Remote Similarity	NPD3666	Approved
0.6627	Remote Similarity	NPD3133	Approved
0.6627	Remote Similarity	NPD3668	Phase 3
0.6579	Remote Similarity	NPD7150	Approved
0.6579	Remote Similarity	NPD7152	Approved
0.6579	Remote Similarity	NPD7151	Approved
0.6543	Remote Similarity	NPD4695	Discontinued
0.6533	Remote Similarity	NPD6922	Approved
0.6533	Remote Similarity	NPD6923	Approved
0.6528	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6406	Remote Similarity	NPD8262	Approved
0.6386	Remote Similarity	NPD4223	Phase 3
0.6386	Remote Similarity	NPD4221	Approved
0.6341	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6903	Approved
0.6322	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6672	Approved
0.6322	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD6079	Approved
0.6279	Remote Similarity	NPD5280	Approved
0.6279	Remote Similarity	NPD4519	Discontinued
0.6279	Remote Similarity	NPD4694	Approved
0.6279	Remote Similarity	NPD4623	Approved
0.6265	Remote Similarity	NPD8028	Phase 2
0.625	Remote Similarity	NPD4194	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD4191	Approved
0.625	Remote Similarity	NPD4192	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.6235	Remote Similarity	NPD4197	Approved
0.623	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3573	Approved
0.6203	Remote Similarity	NPD6926	Approved
0.6203	Remote Similarity	NPD6924	Approved
0.6196	Remote Similarity	NPD4697	Phase 3
0.618	Remote Similarity	NPD5207	Approved
0.6173	Remote Similarity	NPD6932	Approved
0.6163	Remote Similarity	NPD5329	Approved
0.6125	Remote Similarity	NPD8264	Approved
0.6111	Remote Similarity	NPD6411	Approved
0.6111	Remote Similarity	NPD7515	Phase 2
0.6111	Remote Similarity	NPD5694	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6098	Remote Similarity	NPD7145	Approved
0.6098	Remote Similarity	NPD3617	Approved
0.6098	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4690	Approved
0.6092	Remote Similarity	NPD4693	Phase 3
0.6092	Remote Similarity	NPD4138	Approved
0.6092	Remote Similarity	NPD4689	Approved
0.6092	Remote Similarity	NPD4688	Approved
0.6092	Remote Similarity	NPD5690	Phase 2
0.6092	Remote Similarity	NPD5205	Approved
0.6092	Remote Similarity	NPD6098	Approved
0.6087	Remote Similarity	NPD5210	Approved
0.6087	Remote Similarity	NPD4629	Approved
0.6067	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD6933	Approved
0.6044	Remote Similarity	NPD4202	Approved
0.6044	Remote Similarity	NPD6399	Phase 3
0.6022	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5222	Approved
0.6022	Remote Similarity	NPD5221	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD4096	Approved
0.5978	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7748	Approved
0.5978	Remote Similarity	NPD7900	Approved
0.5976	Remote Similarity	NPD5776	Phase 2
0.5976	Remote Similarity	NPD6925	Approved
0.5957	Remote Similarity	NPD3495	Discontinued
0.5957	Remote Similarity	NPD5173	Approved
0.5955	Remote Similarity	NPD4518	Approved
0.5955	Remote Similarity	NPD5208	Approved
0.5952	Remote Similarity	NPD7514	Phase 3
0.5952	Remote Similarity	NPD7332	Phase 2
0.5934	Remote Similarity	NPD7637	Suspended
0.5934	Remote Similarity	NPD6050	Approved
0.593	Remote Similarity	NPD4788	Approved
0.5926	Remote Similarity	NPD7339	Approved
0.5926	Remote Similarity	NPD6942	Approved
0.5909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6673	Approved
0.5889	Remote Similarity	NPD6904	Approved
0.5889	Remote Similarity	NPD6080	Approved
0.5889	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6101	Approved
0.5882	Remote Similarity	NPD6902	Approved
0.5854	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD4195	Approved
0.5833	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5802	Remote Similarity	NPD4785	Approved
0.5802	Remote Similarity	NPD4784	Approved
0.5795	Remote Similarity	NPD1694	Approved
0.5795	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7902	Approved
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD4755	Approved
0.5789	Remote Similarity	NPD6084	Phase 2
0.5773	Remote Similarity	NPD5223	Approved
0.5765	Remote Similarity	NPD6930	Phase 2
0.5765	Remote Similarity	NPD7509	Discontinued
0.5765	Remote Similarity	NPD6931	Approved
0.5761	Remote Similarity	NPD5693	Phase 1
0.575	Remote Similarity	NPD4243	Approved
0.5745	Remote Similarity	NPD5695	Phase 3
0.5745	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD5211	Phase 2
0.5699	Remote Similarity	NPD5779	Approved
0.5699	Remote Similarity	NPD5133	Approved
0.5699	Remote Similarity	NPD7631	Approved
0.5699	Remote Similarity	NPD5778	Approved
0.5698	Remote Similarity	NPD6898	Phase 1
0.5698	Remote Similarity	NPD4139	Approved
0.5698	Remote Similarity	NPD4692	Approved
0.567	Remote Similarity	NPD4700	Approved
0.5657	Remote Similarity	NPD5175	Approved
0.5657	Remote Similarity	NPD5174	Approved
0.5652	Remote Similarity	NPD3672	Approved
0.5652	Remote Similarity	NPD3673	Approved
0.5647	Remote Similarity	NPD7645	Phase 2
0.5638	Remote Similarity	NPD6001	Approved
0.5632	Remote Similarity	NPD5209	Approved
0.56	Remote Similarity	NPD5141	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