NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	271.747
LogP:	3.861
LogD:	3.441
LogS:	-2.772
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.487
Fsp3:	0.733
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:	-4.353
MDCK Permeability:	2.0376550310174935e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.17
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.403
30% Bioavailability (F30%):	0.272

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.699
Plasma Protein Binding (PPB):	93.45738983154297%
Volume Distribution (VD):	1.434
Pgp-substrate:	5.609479904174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.151
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.657
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	11.131
Half-life (T1/2):	0.389

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.432
Carcinogencity:	0.209
Eye Corrosion:	0.203
Eye Irritation:	0.826
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC267027

Natural Product ID:	NPC267027
*Common Name:**	2,3-Dihydroxybisabola-4,10-Diene
IUPAC Name:	(1S,2S,5R)-2-methyl-5-[(2S)-6-methylhept-5-en-2-yl]cyclohex-3-ene-1,2-diol
Synonyms:
Standard InCHIKey:	YRFJMOGROZTYPC-XGUBFFRZSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-11(2)6-5-7-12(3)13-8-9-15(4,17)14(16)10-13/h6,8-9,12-14,16-17H,5,7,10H2,1-4H3/t12-,13+,14-,15-/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@@H]1C=C[C@@](C)([C@H](C1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1775016
PubChem CID:	14633006
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
NPO31410	Cupania cinerea	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[21438586]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90000.0	nM	PMID[559028]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	20000.0	nM	PMID[559028]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	61300.0	nM	PMID[559028]

☑ 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 NPC267027 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	160
0.1-0.2	1366
0.2-0.3	6447
0.3-0.4	17010
0.4-0.5	9908
0.5-0.6	5948
0.6-0.7	1534
0.7-0.8	275
0.8-0.85	35
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC326310
0.8923	High Similarity	NPC82337
0.8871	High Similarity	NPC66020
0.875	High Similarity	NPC300593
0.8657	High Similarity	NPC473893
0.8615	High Similarity	NPC471200
0.8485	Intermediate Similarity	NPC311736
0.8485	Intermediate Similarity	NPC202017
0.8438	Intermediate Similarity	NPC207007
0.8438	Intermediate Similarity	NPC68679
0.8438	Intermediate Similarity	NPC321867
0.8413	Intermediate Similarity	NPC122239
0.8382	Intermediate Similarity	NPC471560
0.8361	Intermediate Similarity	NPC227135
0.8358	Intermediate Similarity	NPC163290
0.8308	Intermediate Similarity	NPC473508
0.8286	Intermediate Similarity	NPC220939
0.8286	Intermediate Similarity	NPC265485
0.8281	Intermediate Similarity	NPC240506
0.8281	Intermediate Similarity	NPC99487
0.8254	Intermediate Similarity	NPC155025
0.8219	Intermediate Similarity	NPC167891
0.8219	Intermediate Similarity	NPC83351
0.8154	Intermediate Similarity	NPC225342
0.8143	Intermediate Similarity	NPC242992
0.8143	Intermediate Similarity	NPC23954
0.8143	Intermediate Similarity	NPC471268
0.8143	Intermediate Similarity	NPC471271
0.8125	Intermediate Similarity	NPC475931
0.8088	Intermediate Similarity	NPC114651
0.8088	Intermediate Similarity	NPC73603
0.8082	Intermediate Similarity	NPC40049
0.8065	Intermediate Similarity	NPC130209
0.8065	Intermediate Similarity	NPC148216
0.8065	Intermediate Similarity	NPC148163
0.806	Intermediate Similarity	NPC308844
0.806	Intermediate Similarity	NPC287339
0.803	Intermediate Similarity	NPC174956
0.8028	Intermediate Similarity	NPC130665
0.8	Intermediate Similarity	NPC34834
0.7973	Intermediate Similarity	NPC475980
0.7971	Intermediate Similarity	NPC471238
0.7971	Intermediate Similarity	NPC224532
0.7971	Intermediate Similarity	NPC96484
0.7969	Intermediate Similarity	NPC226848
0.7969	Intermediate Similarity	NPC181872
0.7945	Intermediate Similarity	NPC170148
0.7945	Intermediate Similarity	NPC265588
0.7917	Intermediate Similarity	NPC190859
0.7887	Intermediate Similarity	NPC477792
0.7887	Intermediate Similarity	NPC471272
0.7857	Intermediate Similarity	NPC74722
0.7857	Intermediate Similarity	NPC474248
0.7857	Intermediate Similarity	NPC304690
0.7838	Intermediate Similarity	NPC91594
0.7826	Intermediate Similarity	NPC136813
0.7826	Intermediate Similarity	NPC477791
0.7794	Intermediate Similarity	NPC473722
0.7792	Intermediate Similarity	NPC471408
0.7778	Intermediate Similarity	NPC232247
0.7778	Intermediate Similarity	NPC251666
0.7763	Intermediate Similarity	NPC474592
0.7761	Intermediate Similarity	NPC474155
0.7761	Intermediate Similarity	NPC83200
0.7761	Intermediate Similarity	NPC473759
0.7714	Intermediate Similarity	NPC305698
0.7714	Intermediate Similarity	NPC167527
0.7703	Intermediate Similarity	NPC126969
0.7703	Intermediate Similarity	NPC256720
0.7703	Intermediate Similarity	NPC236228
0.7703	Intermediate Similarity	NPC253190
0.7692	Intermediate Similarity	NPC474634
0.7681	Intermediate Similarity	NPC250977
0.7671	Intermediate Similarity	NPC471525
0.7662	Intermediate Similarity	NPC264245
0.7662	Intermediate Similarity	NPC471270
0.7656	Intermediate Similarity	NPC48891
0.7647	Intermediate Similarity	NPC107540
0.7647	Intermediate Similarity	NPC96793
0.7647	Intermediate Similarity	NPC309300
0.7647	Intermediate Similarity	NPC290367
0.7647	Intermediate Similarity	NPC323424
0.7639	Intermediate Similarity	NPC242001
0.7632	Intermediate Similarity	NPC233295
0.7625	Intermediate Similarity	NPC281316
0.7612	Intermediate Similarity	NPC475251
0.7606	Intermediate Similarity	NPC217570
0.7606	Intermediate Similarity	NPC329989
0.7606	Intermediate Similarity	NPC90115
0.7606	Intermediate Similarity	NPC239373
0.76	Intermediate Similarity	NPC477426
0.76	Intermediate Similarity	NPC476007
0.76	Intermediate Similarity	NPC476703
0.76	Intermediate Similarity	NPC477427
0.76	Intermediate Similarity	NPC477425
0.76	Intermediate Similarity	NPC474826
0.7595	Intermediate Similarity	NPC83702
0.7581	Intermediate Similarity	NPC40417
0.7581	Intermediate Similarity	NPC157781
0.7581	Intermediate Similarity	NPC181255
0.7581	Intermediate Similarity	NPC35519
0.7581	Intermediate Similarity	NPC306195
0.7581	Intermediate Similarity	NPC294358
0.7581	Intermediate Similarity	NPC179169
0.7571	Intermediate Similarity	NPC472255
0.7571	Intermediate Similarity	NPC68703
0.7571	Intermediate Similarity	NPC69649
0.7571	Intermediate Similarity	NPC472253
0.7571	Intermediate Similarity	NPC171225
0.7571	Intermediate Similarity	NPC259299
0.7568	Intermediate Similarity	NPC23231
0.7568	Intermediate Similarity	NPC69383
0.7568	Intermediate Similarity	NPC66566
0.7568	Intermediate Similarity	NPC477923
0.7568	Intermediate Similarity	NPC313179
0.7568	Intermediate Similarity	NPC60818
0.7568	Intermediate Similarity	NPC171148
0.7564	Intermediate Similarity	NPC472465
0.7564	Intermediate Similarity	NPC49964
0.7538	Intermediate Similarity	NPC52012
0.7536	Intermediate Similarity	NPC19569
0.7534	Intermediate Similarity	NPC471799
0.7534	Intermediate Similarity	NPC329763
0.7532	Intermediate Similarity	NPC234193
0.7532	Intermediate Similarity	NPC95124
0.7532	Intermediate Similarity	NPC113024
0.7532	Intermediate Similarity	NPC241290
0.7532	Intermediate Similarity	NPC164840
0.7532	Intermediate Similarity	NPC471266
0.7532	Intermediate Similarity	NPC236707
0.7532	Intermediate Similarity	NPC96362
0.7532	Intermediate Similarity	NPC209944
0.75	Intermediate Similarity	NPC129630
0.75	Intermediate Similarity	NPC471781
0.75	Intermediate Similarity	NPC92801
0.75	Intermediate Similarity	NPC145498
0.75	Intermediate Similarity	NPC281590
0.75	Intermediate Similarity	NPC477089
0.75	Intermediate Similarity	NPC189745
0.75	Intermediate Similarity	NPC476314
0.75	Intermediate Similarity	NPC81615
0.7468	Intermediate Similarity	NPC23748
0.7468	Intermediate Similarity	NPC317458
0.7467	Intermediate Similarity	NPC315261
0.7467	Intermediate Similarity	NPC310643
0.7467	Intermediate Similarity	NPC477925
0.7467	Intermediate Similarity	NPC274079
0.7465	Intermediate Similarity	NPC272961
0.7465	Intermediate Similarity	NPC117804
0.7465	Intermediate Similarity	NPC208999
0.7436	Intermediate Similarity	NPC47761
0.7436	Intermediate Similarity	NPC249423
0.7436	Intermediate Similarity	NPC311891
0.7436	Intermediate Similarity	NPC476646
0.7432	Intermediate Similarity	NPC477138
0.7432	Intermediate Similarity	NPC471797
0.7432	Intermediate Similarity	NPC306727
0.7432	Intermediate Similarity	NPC476366
0.7432	Intermediate Similarity	NPC243342
0.7432	Intermediate Similarity	NPC201048
0.7429	Intermediate Similarity	NPC476406
0.7429	Intermediate Similarity	NPC279434
0.7429	Intermediate Similarity	NPC272125
0.7424	Intermediate Similarity	NPC475830
0.7419	Intermediate Similarity	NPC26906
0.7419	Intermediate Similarity	NPC214584
0.7419	Intermediate Similarity	NPC244038
0.7407	Intermediate Similarity	NPC255143
0.7403	Intermediate Similarity	NPC84694
0.7403	Intermediate Similarity	NPC476701
0.7403	Intermediate Similarity	NPC81306
0.7403	Intermediate Similarity	NPC109546
0.7403	Intermediate Similarity	NPC28862
0.7403	Intermediate Similarity	NPC328714
0.7403	Intermediate Similarity	NPC47982
0.7403	Intermediate Similarity	NPC143182
0.7397	Intermediate Similarity	NPC471662
0.7397	Intermediate Similarity	NPC164022
0.7397	Intermediate Similarity	NPC469343
0.7391	Intermediate Similarity	NPC225415
0.7391	Intermediate Similarity	NPC110241
0.7385	Intermediate Similarity	NPC274396
0.7385	Intermediate Similarity	NPC24443
0.7375	Intermediate Similarity	NPC238485
0.7375	Intermediate Similarity	NPC205845
0.7375	Intermediate Similarity	NPC185568
0.7368	Intermediate Similarity	NPC470758
0.7368	Intermediate Similarity	NPC74995
0.7368	Intermediate Similarity	NPC477924
0.7368	Intermediate Similarity	NPC470711
0.7361	Intermediate Similarity	NPC9942
0.7349	Intermediate Similarity	NPC115607
0.7349	Intermediate Similarity	NPC49783
0.7342	Intermediate Similarity	NPC477385
0.7342	Intermediate Similarity	NPC477390
0.7342	Intermediate Similarity	NPC50964
0.7342	Intermediate Similarity	NPC87489
0.7333	Intermediate Similarity	NPC133580
0.7333	Intermediate Similarity	NPC114236
0.7333	Intermediate Similarity	NPC476605

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 NPC267027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	2017
0.2-0.3	3857
0.3-0.4	2202
0.4-0.5	694
0.5-0.6	163
0.6-0.7	62
0.7-0.8	1
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD368	Approved
0.8065	Intermediate Similarity	NPD342	Phase 1
0.7568	Intermediate Similarity	NPD8264	Approved
0.7467	Intermediate Similarity	NPD6933	Approved
0.7273	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6924	Approved
0.72	Intermediate Similarity	NPD6926	Approved
0.7089	Intermediate Similarity	NPD7514	Phase 3
0.7089	Intermediate Similarity	NPD7332	Phase 2
0.7089	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD6931	Approved
0.7013	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6929	Approved
0.6905	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7524	Approved
0.6883	Remote Similarity	NPD6942	Approved
0.6883	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4819	Approved
0.6875	Remote Similarity	NPD4822	Approved
0.6875	Remote Similarity	NPD4820	Approved
0.6866	Remote Similarity	NPD4219	Approved
0.6842	Remote Similarity	NPD4732	Discontinued
0.6835	Remote Similarity	NPD7145	Approved
0.6829	Remote Similarity	NPD6695	Phase 3
0.68	Remote Similarity	NPD7144	Approved
0.68	Remote Similarity	NPD7143	Approved
0.679	Remote Similarity	NPD6902	Approved
0.6747	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7151	Approved
0.6711	Remote Similarity	NPD7150	Approved
0.6711	Remote Similarity	NPD7152	Approved
0.6709	Remote Similarity	NPD5776	Phase 2
0.6709	Remote Similarity	NPD6932	Approved
0.6709	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6627	Remote Similarity	NPD5362	Discontinued
0.6627	Remote Similarity	NPD5332	Approved
0.6627	Remote Similarity	NPD5331	Approved
0.6625	Remote Similarity	NPD4268	Approved
0.6625	Remote Similarity	NPD4271	Approved
0.6585	Remote Similarity	NPD4790	Discontinued
0.6585	Remote Similarity	NPD6898	Phase 1
0.6543	Remote Similarity	NPD7645	Phase 2
0.6538	Remote Similarity	NPD4785	Approved
0.6538	Remote Similarity	NPD4784	Approved
0.6517	Remote Similarity	NPD5778	Approved
0.6517	Remote Similarity	NPD5779	Approved
0.6512	Remote Similarity	NPD7750	Discontinued
0.6506	Remote Similarity	NPD4269	Approved
0.6506	Remote Similarity	NPD3667	Approved
0.6506	Remote Similarity	NPD4270	Approved
0.6463	Remote Similarity	NPD7525	Registered
0.6463	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7154	Phase 3
0.642	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5344	Discontinued
0.6353	Remote Similarity	NPD4786	Approved
0.6349	Remote Similarity	NPD4265	Approved
0.6341	Remote Similarity	NPD6683	Phase 2
0.6292	Remote Similarity	NPD7838	Discovery
0.6282	Remote Similarity	NPD4243	Approved
0.6279	Remote Similarity	NPD5363	Approved
0.6279	Remote Similarity	NPD1696	Phase 3
0.6267	Remote Similarity	NPD7331	Phase 2
0.6265	Remote Similarity	NPD4252	Approved
0.6265	Remote Similarity	NPD4748	Discontinued
0.6235	Remote Similarity	NPD6110	Phase 1
0.6222	Remote Similarity	NPD7087	Discontinued
0.6222	Remote Similarity	NPD7983	Approved
0.6207	Remote Similarity	NPD5786	Approved
0.6207	Remote Similarity	NPD4519	Discontinued
0.6207	Remote Similarity	NPD4623	Approved
0.619	Remote Similarity	NPD5369	Approved
0.618	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6101	Approved
0.617	Remote Similarity	NPD4225	Approved
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3666	Approved
0.6145	Remote Similarity	NPD4195	Approved
0.6133	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7341	Phase 2
0.6111	Remote Similarity	NPD6698	Approved
0.6111	Remote Similarity	NPD46	Approved
0.6049	Remote Similarity	NPD4190	Phase 3
0.6049	Remote Similarity	NPD5275	Approved
0.6044	Remote Similarity	NPD6411	Approved
0.6044	Remote Similarity	NPD7637	Suspended
0.6027	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD1145	Discontinued
0.6023	Remote Similarity	NPD3618	Phase 1
0.6023	Remote Similarity	NPD5279	Phase 3
0.6023	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD385	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD384	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4250	Approved
0.5955	Remote Similarity	NPD4251	Approved
0.5946	Remote Similarity	NPD4192	Approved
0.5946	Remote Similarity	NPD4191	Approved
0.5946	Remote Similarity	NPD4193	Approved
0.5946	Remote Similarity	NPD4194	Approved
0.5938	Remote Similarity	NPD6648	Approved
0.5934	Remote Similarity	NPD7136	Phase 2
0.5934	Remote Similarity	NPD5785	Approved
0.5909	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4695	Discontinued
0.5882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5368	Approved
0.587	Remote Similarity	NPD6079	Approved
0.5824	Remote Similarity	NPD5328	Approved
0.5824	Remote Similarity	NPD4753	Phase 2
0.5823	Remote Similarity	NPD15	Approved
0.5823	Remote Similarity	NPD791	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5806	Remote Similarity	NPD4202	Approved
0.5795	Remote Similarity	NPD3668	Phase 3
0.5789	Remote Similarity	NPD7839	Suspended
0.5783	Remote Similarity	NPD1346	Approved
0.5761	Remote Similarity	NPD3168	Discontinued
0.5747	Remote Similarity	NPD6435	Approved
0.5747	Remote Similarity	NPD4221	Approved
0.5747	Remote Similarity	NPD4223	Phase 3
0.5745	Remote Similarity	NPD5282	Discontinued
0.573	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD4518	Approved
0.5714	Remote Similarity	NPD4159	Approved
0.5701	Remote Similarity	NPD7115	Discovery
0.57	Remote Similarity	NPD5141	Approved
0.5699	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7515	Phase 2
0.5684	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5210	Approved
0.5684	Remote Similarity	NPD4629	Approved
0.5673	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5690	Phase 2
0.5663	Remote Similarity	NPD8039	Approved
0.5658	Remote Similarity	NPD3210	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6051	Approved
0.5652	Remote Similarity	NPD5370	Suspended
0.5644	Remote Similarity	NPD6640	Phase 3
0.5638	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD5222	Approved
0.5625	Remote Similarity	NPD1082	Approved
0.5625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5221	Approved
0.5618	Remote Similarity	NPD4197	Approved
0.5612	Remote Similarity	NPD5286	Approved
0.5612	Remote Similarity	NPD7640	Approved
0.5612	Remote Similarity	NPD4696	Approved
0.5612	Remote Similarity	NPD5285	Approved
0.5612	Remote Similarity	NPD7639	Approved
0.5606	Remote Similarity	NPD386	Approved
0.5606	Remote Similarity	NPD388	Approved
0.56	Remote Similarity	NPD5700	Clinical (unspecified phase)

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