NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	271.747
LogP:	3.988
LogD:	3.74
LogS:	-3.018
# 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:	4.225
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:	-4.541
MDCK Permeability:	1.1199967048014514e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.273
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.678
Plasma Protein Binding (PPB):	94.0134506225586%
Volume Distribution (VD):	1.217
Pgp-substrate:	5.469110488891602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.096
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.733
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	14.773
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.74
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.162
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.068
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC326310

Natural Product ID:	NPC326310
*Common Name:**	1,2-Dihydroxybisabola-3,10-Diene
IUPAC Name:	3-methyl-6-(6-methylhept-5-en-2-yl)cyclohex-3-ene-1,2-diol
Synonyms:
Standard InCHIKey:	SDAWXTDBEYZMMX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H26O2/c1-10(2)6-5-7-11(3)13-9-8-12(4)14(16)15(13)17/h6,8,11,13-17H,5,7,9H2,1-4H3
SMILES:	CC1=CCC(C(C1O)O)C(C)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1775015
PubChem CID:	52951624
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[454518]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	20000.0	nM	PMID[454518]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	38200.0	nM	PMID[454518]

☑ 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 NPC326310 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	154
0.1-0.2	1476
0.2-0.3	7316
0.3-0.4	17260
0.4-0.5	9317
0.5-0.6	5477
0.6-0.7	1400
0.7-0.8	249
0.8-0.85	31
0.85-0.9	14
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC267027
0.873	High Similarity	NPC207007
0.873	High Similarity	NPC321867
0.873	High Similarity	NPC68679
0.8636	High Similarity	NPC82337
0.8571	High Similarity	NPC66020
0.8551	High Similarity	NPC265485
0.8551	High Similarity	NPC220939
0.8485	Intermediate Similarity	NPC311736
0.8485	Intermediate Similarity	NPC202017
0.8413	Intermediate Similarity	NPC122239
0.8406	Intermediate Similarity	NPC23954
0.8406	Intermediate Similarity	NPC242992
0.8382	Intermediate Similarity	NPC473893
0.8361	Intermediate Similarity	NPC232247
0.8361	Intermediate Similarity	NPC251666
0.8358	Intermediate Similarity	NPC163290
0.8358	Intermediate Similarity	NPC114651
0.8333	Intermediate Similarity	NPC471200
0.8333	Intermediate Similarity	NPC287339
0.8308	Intermediate Similarity	NPC473508
0.8281	Intermediate Similarity	NPC240506
0.8281	Intermediate Similarity	NPC99487
0.8254	Intermediate Similarity	NPC155025
0.8235	Intermediate Similarity	NPC96484
0.8182	Intermediate Similarity	NPC323424
0.8182	Intermediate Similarity	NPC96793
0.8143	Intermediate Similarity	NPC477792
0.8143	Intermediate Similarity	NPC471268
0.8143	Intermediate Similarity	NPC471271
0.8116	Intermediate Similarity	NPC471560
0.8082	Intermediate Similarity	NPC91594
0.8065	Intermediate Similarity	NPC130209
0.8065	Intermediate Similarity	NPC148216
0.8065	Intermediate Similarity	NPC148163
0.8	Intermediate Similarity	NPC34834
0.8	Intermediate Similarity	NPC92801
0.7973	Intermediate Similarity	NPC83351
0.7973	Intermediate Similarity	NPC167891
0.7969	Intermediate Similarity	NPC226848
0.7945	Intermediate Similarity	NPC265588
0.791	Intermediate Similarity	NPC300593
0.7857	Intermediate Similarity	NPC474248
0.7846	Intermediate Similarity	NPC475931
0.7838	Intermediate Similarity	NPC477427
0.7838	Intermediate Similarity	NPC477425
0.7838	Intermediate Similarity	NPC474826
0.7838	Intermediate Similarity	NPC40049
0.7838	Intermediate Similarity	NPC477426
0.7808	Intermediate Similarity	NPC477923
0.7808	Intermediate Similarity	NPC66566
0.7792	Intermediate Similarity	NPC471408
0.7778	Intermediate Similarity	NPC234527
0.7778	Intermediate Similarity	NPC227135
0.7778	Intermediate Similarity	NPC14352
0.7778	Intermediate Similarity	NPC67508
0.7778	Intermediate Similarity	NPC84824
0.7761	Intermediate Similarity	NPC474155
0.7761	Intermediate Similarity	NPC473759
0.7761	Intermediate Similarity	NPC83200
0.7714	Intermediate Similarity	NPC471238
0.7714	Intermediate Similarity	NPC224532
0.7705	Intermediate Similarity	NPC244038
0.7692	Intermediate Similarity	NPC317458
0.7671	Intermediate Similarity	NPC201048
0.7671	Intermediate Similarity	NPC476366
0.7662	Intermediate Similarity	NPC476646
0.7656	Intermediate Similarity	NPC48891
0.7647	Intermediate Similarity	NPC225415
0.7647	Intermediate Similarity	NPC290367
0.7647	Intermediate Similarity	NPC107540
0.7639	Intermediate Similarity	NPC471272
0.7639	Intermediate Similarity	NPC164022
0.7625	Intermediate Similarity	NPC255143
0.7612	Intermediate Similarity	NPC225342
0.76	Intermediate Similarity	NPC470711
0.76	Intermediate Similarity	NPC477924
0.76	Intermediate Similarity	NPC470758
0.76	Intermediate Similarity	NPC130136
0.7595	Intermediate Similarity	NPC185568
0.7595	Intermediate Similarity	NPC83702
0.7581	Intermediate Similarity	NPC157781
0.7581	Intermediate Similarity	NPC179169
0.7581	Intermediate Similarity	NPC181255
0.7581	Intermediate Similarity	NPC35519
0.7581	Intermediate Similarity	NPC306195
0.7571	Intermediate Similarity	NPC477791
0.7571	Intermediate Similarity	NPC171225
0.7568	Intermediate Similarity	NPC69383
0.7568	Intermediate Similarity	NPC32832
0.7568	Intermediate Similarity	NPC171148
0.7568	Intermediate Similarity	NPC313179
0.7568	Intermediate Similarity	NPC313185
0.7536	Intermediate Similarity	NPC308844
0.7534	Intermediate Similarity	NPC130665
0.7532	Intermediate Similarity	NPC295131
0.7532	Intermediate Similarity	NPC96362
0.75	Intermediate Similarity	NPC13823
0.75	Intermediate Similarity	NPC189745
0.75	Intermediate Similarity	NPC476314
0.75	Intermediate Similarity	NPC68119
0.75	Intermediate Similarity	NPC174956
0.7468	Intermediate Similarity	NPC57370
0.7468	Intermediate Similarity	NPC474634
0.7467	Intermediate Similarity	NPC253190
0.7467	Intermediate Similarity	NPC170148
0.7467	Intermediate Similarity	NPC470749
0.7467	Intermediate Similarity	NPC477925
0.7467	Intermediate Similarity	NPC274079
0.7467	Intermediate Similarity	NPC236228
0.7467	Intermediate Similarity	NPC256720
0.7465	Intermediate Similarity	NPC305698
0.7465	Intermediate Similarity	NPC167527
0.7465	Intermediate Similarity	NPC208999
0.7436	Intermediate Similarity	NPC474531
0.7436	Intermediate Similarity	NPC471270
0.7432	Intermediate Similarity	NPC190859
0.7432	Intermediate Similarity	NPC477138
0.7432	Intermediate Similarity	NPC306727
0.7432	Intermediate Similarity	NPC243342
0.7429	Intermediate Similarity	NPC250977
0.7424	Intermediate Similarity	NPC181872
0.7419	Intermediate Similarity	NPC26906
0.7419	Intermediate Similarity	NPC214584
0.7407	Intermediate Similarity	NPC281316
0.7403	Intermediate Similarity	NPC84694
0.7403	Intermediate Similarity	NPC30986
0.7403	Intermediate Similarity	NPC109546
0.7403	Intermediate Similarity	NPC81306
0.7403	Intermediate Similarity	NPC281138
0.7403	Intermediate Similarity	NPC209430
0.7403	Intermediate Similarity	NPC28862
0.7403	Intermediate Similarity	NPC143182
0.7403	Intermediate Similarity	NPC47982
0.7397	Intermediate Similarity	NPC242001
0.7397	Intermediate Similarity	NPC167706
0.7397	Intermediate Similarity	NPC469343
0.7391	Intermediate Similarity	NPC309300
0.7375	Intermediate Similarity	NPC302360
0.7368	Intermediate Similarity	NPC471798
0.7361	Intermediate Similarity	NPC90115
0.7361	Intermediate Similarity	NPC217570
0.7353	Intermediate Similarity	NPC282694
0.7353	Intermediate Similarity	NPC79576
0.7353	Intermediate Similarity	NPC194208
0.7353	Intermediate Similarity	NPC475251
0.7349	Intermediate Similarity	NPC470361
0.7342	Intermediate Similarity	NPC202389
0.7342	Intermediate Similarity	NPC101462
0.7342	Intermediate Similarity	NPC87489
0.7342	Intermediate Similarity	NPC49964
0.7333	Intermediate Similarity	NPC291503
0.7333	Intermediate Similarity	NPC133580
0.7324	Intermediate Similarity	NPC136813
0.7324	Intermediate Similarity	NPC96962
0.7324	Intermediate Similarity	NPC259299
0.7324	Intermediate Similarity	NPC68703
0.7324	Intermediate Similarity	NPC69649
0.7324	Intermediate Similarity	NPC73603
0.7317	Intermediate Similarity	NPC245004
0.7317	Intermediate Similarity	NPC470620
0.7308	Intermediate Similarity	NPC471266
0.7308	Intermediate Similarity	NPC236112
0.7308	Intermediate Similarity	NPC148685
0.7308	Intermediate Similarity	NPC206062
0.7308	Intermediate Similarity	NPC104120
0.7308	Intermediate Similarity	NPC236707
0.7308	Intermediate Similarity	NPC172013
0.7308	Intermediate Similarity	NPC474592
0.7308	Intermediate Similarity	NPC234193
0.7308	Intermediate Similarity	NPC287749
0.7308	Intermediate Similarity	NPC95124
0.7308	Intermediate Similarity	NPC157895
0.7302	Intermediate Similarity	NPC177112
0.7302	Intermediate Similarity	NPC71506
0.7297	Intermediate Similarity	NPC182717
0.7297	Intermediate Similarity	NPC471799
0.7286	Intermediate Similarity	NPC2728
0.7286	Intermediate Similarity	NPC60837
0.7286	Intermediate Similarity	NPC282619
0.7286	Intermediate Similarity	NPC172613
0.7286	Intermediate Similarity	NPC19569
0.7286	Intermediate Similarity	NPC473722
0.7286	Intermediate Similarity	NPC258595
0.7286	Intermediate Similarity	NPC208198
0.7286	Intermediate Similarity	NPC11555
0.7284	Intermediate Similarity	NPC35933
0.7273	Intermediate Similarity	NPC22955
0.7273	Intermediate Similarity	NPC474989
0.7273	Intermediate Similarity	NPC275910
0.7273	Intermediate Similarity	NPC52012
0.7273	Intermediate Similarity	NPC11908
0.7273	Intermediate Similarity	NPC475980
0.7273	Intermediate Similarity	NPC478122
0.7273	Intermediate Similarity	NPC470396
0.7273	Intermediate Similarity	NPC172066
0.7273	Intermediate Similarity	NPC99168
0.7273	Intermediate Similarity	NPC474216
0.7273	Intermediate Similarity	NPC475994
0.7262	Intermediate Similarity	NPC473099

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 NPC326310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	2124
0.2-0.3	3915
0.3-0.4	2127
0.4-0.5	646
0.5-0.6	131
0.6-0.7	57
0.7-0.8	0
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
0.873	High Similarity	NPD368	Approved
0.8065	Intermediate Similarity	NPD342	Phase 1
0.7568	Intermediate Similarity	NPD8264	Approved
0.7013	Intermediate Similarity	NPD6933	Approved
0.7013	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7645	Phase 2
0.6883	Remote Similarity	NPD6942	Approved
0.6883	Remote Similarity	NPD7339	Approved
0.6835	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6926	Approved
0.6753	Remote Similarity	NPD6924	Approved
0.675	Remote Similarity	NPD6929	Approved
0.6709	Remote Similarity	NPD5776	Phase 2
0.6709	Remote Similarity	NPD6925	Approved
0.6706	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6625	Remote Similarity	NPD7145	Approved
0.6618	Remote Similarity	NPD4219	Approved
0.6585	Remote Similarity	NPD6902	Approved
0.6579	Remote Similarity	NPD7144	Approved
0.6579	Remote Similarity	NPD7143	Approved
0.6512	Remote Similarity	NPD7524	Approved
0.6508	Remote Similarity	NPD384	Approved
0.6508	Remote Similarity	NPD385	Approved
0.6506	Remote Similarity	NPD3667	Approved
0.6494	Remote Similarity	NPD7151	Approved
0.6494	Remote Similarity	NPD7150	Approved
0.6494	Remote Similarity	NPD7152	Approved
0.6471	Remote Similarity	NPD1696	Phase 3
0.6463	Remote Similarity	NPD7509	Discontinued
0.6463	Remote Similarity	NPD4819	Approved
0.6463	Remote Similarity	NPD4820	Approved
0.6463	Remote Similarity	NPD4822	Approved
0.6463	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD6695	Phase 3
0.6429	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD5331	Approved
0.642	Remote Similarity	NPD4271	Approved
0.642	Remote Similarity	NPD4268	Approved
0.641	Remote Similarity	NPD4732	Discontinued
0.6395	Remote Similarity	NPD3618	Phase 1
0.6386	Remote Similarity	NPD4790	Discontinued
0.6386	Remote Similarity	NPD6898	Phase 1
0.6353	Remote Similarity	NPD4786	Approved
0.6353	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4265	Approved
0.6344	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD5778	Approved
0.631	Remote Similarity	NPD4270	Approved
0.631	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD6932	Approved
0.6279	Remote Similarity	NPD6893	Approved
0.6265	Remote Similarity	NPD4748	Discontinued
0.6265	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD6110	Phase 1
0.6235	Remote Similarity	NPD7154	Phase 3
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5344	Discontinued
0.618	Remote Similarity	NPD5328	Approved
0.6163	Remote Similarity	NPD3133	Approved
0.6163	Remote Similarity	NPD3665	Phase 1
0.6163	Remote Similarity	NPD3666	Approved
0.6145	Remote Similarity	NPD6683	Phase 2
0.6136	Remote Similarity	NPD7750	Discontinued
0.6125	Remote Similarity	NPD4785	Approved
0.6125	Remote Similarity	NPD4784	Approved
0.6111	Remote Similarity	NPD6698	Approved
0.6111	Remote Similarity	NPD46	Approved
0.6092	Remote Similarity	NPD5363	Approved
0.6076	Remote Similarity	NPD4243	Approved
0.6071	Remote Similarity	NPD4252	Approved
0.6053	Remote Similarity	NPD7331	Phase 2
0.6044	Remote Similarity	NPD6079	Approved
0.6044	Remote Similarity	NPD7515	Phase 2
0.6044	Remote Similarity	NPD7983	Approved
0.6023	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5978	Remote Similarity	NPD4202	Approved
0.5977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7639	Approved
0.5938	Remote Similarity	NPD7640	Approved
0.5934	Remote Similarity	NPD7838	Discovery
0.5921	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4159	Approved
0.587	Remote Similarity	NPD6411	Approved
0.587	Remote Similarity	NPD7637	Suspended
0.587	Remote Similarity	NPD7087	Discontinued
0.5854	Remote Similarity	NPD4190	Phase 3
0.5854	Remote Similarity	NPD5275	Approved
0.5843	Remote Similarity	NPD4623	Approved
0.5843	Remote Similarity	NPD5279	Phase 3
0.5843	Remote Similarity	NPD4249	Approved
0.5843	Remote Similarity	NPD4519	Discontinued
0.5833	Remote Similarity	NPD7638	Approved
0.5823	Remote Similarity	NPD15	Approved
0.5823	Remote Similarity	NPD791	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5814	Remote Similarity	NPD5369	Approved
0.5811	Remote Similarity	NPD1145	Discontinued
0.5811	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3668	Phase 3
0.5789	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5222	Approved
0.5789	Remote Similarity	NPD3197	Phase 1
0.5789	Remote Similarity	NPD4697	Phase 3
0.5789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5221	Approved
0.5789	Remote Similarity	NPD371	Approved
0.5778	Remote Similarity	NPD4250	Approved
0.5778	Remote Similarity	NPD4251	Approved
0.5773	Remote Similarity	NPD6648	Approved
0.5765	Remote Similarity	NPD4195	Approved
0.5761	Remote Similarity	NPD7136	Phase 2
0.5761	Remote Similarity	NPD3168	Discontinued
0.5761	Remote Similarity	NPD5785	Approved
0.5753	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD7748	Approved
0.5733	Remote Similarity	NPD4192	Approved
0.5733	Remote Similarity	NPD4191	Approved
0.5733	Remote Similarity	NPD4194	Approved
0.5733	Remote Similarity	NPD4193	Approved
0.5729	Remote Similarity	NPD4755	Approved
0.5729	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD7341	Phase 2
0.5701	Remote Similarity	NPD7115	Discovery
0.57	Remote Similarity	NPD5141	Approved
0.5698	Remote Similarity	NPD5368	Approved
0.5698	Remote Similarity	NPD4695	Discontinued
0.567	Remote Similarity	NPD5290	Discontinued
0.567	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4753	Phase 2
0.5644	Remote Similarity	NPD6640	Phase 3
0.5638	Remote Similarity	NPD6399	Phase 3
0.5625	Remote Similarity	NPD1082	Approved
0.5625	Remote Similarity	NPD7839	Suspended
0.5612	Remote Similarity	NPD5286	Approved
0.5612	Remote Similarity	NPD4696	Approved
0.5612	Remote Similarity	NPD5285	Approved
0.5612	Remote Similarity	NPD4700	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