NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	266.708
LogP:	3.288
LogD:	1.902
LogS:	-3.523
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	3.426
Fsp3:	0.533
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:	-4.623
MDCK Permeability:	1.8435564925312065e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	80.40673065185547%
Volume Distribution (VD):	0.285
Pgp-substrate:	18.305320739746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.33
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	1.373
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.234
Skin Sensitization:	0.061
Carcinogencity:	0.054
Eye Corrosion:	0.004
Eye Irritation:	0.179
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC186933

Natural Product ID:	NPC186933
*Common Name:**	1Alpha-Hydroxy-4Alphah-1,2,3,4-Tetrahydrocadalen-15-Oic Acid
IUPAC Name:	(5R,8S)-5-hydroxy-5-methyl-8-propan-2-yl-7,8-dihydro-6H-naphthalene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	WOURYSLHFFSMAH-XHDPSFHLSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9(2)11-6-7-15(3,18)13-5-4-10(14(16)17)8-12(11)13/h4-5,8-9,11,18H,6-7H2,1-3H3,(H,16,17)/t11-,15+/m0/s1
SMILES:	CC([C@@H]1CC[C@@](c2c1cc(cc2)C(=O)O)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459412
PubChem CID:	21592236
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
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO25769	Heterotheca inuloides	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	24.6	%	PMID[492303]

☑ 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 NPC186933 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	245
0.1-0.2	1260
0.2-0.3	2458
0.3-0.4	7098
0.4-0.5	12748
0.5-0.6	11540
0.6-0.7	6166
0.7-0.8	1093
0.8-0.85	59
0.85-0.9	24
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9352	High Similarity	NPC66208
0.9083	High Similarity	NPC474057
0.9074	High Similarity	NPC318327
0.8879	High Similarity	NPC472222
0.8879	High Similarity	NPC472221
0.8868	High Similarity	NPC304873
0.8803	High Similarity	NPC167323
0.8803	High Similarity	NPC269923
0.8796	High Similarity	NPC105899
0.8785	High Similarity	NPC255676
0.8739	High Similarity	NPC133308
0.8739	High Similarity	NPC95126
0.8739	High Similarity	NPC475002
0.8692	High Similarity	NPC25458
0.8679	High Similarity	NPC217621
0.8655	High Similarity	NPC85511
0.8655	High Similarity	NPC275145
0.8609	High Similarity	NPC158157
0.8596	High Similarity	NPC476357
0.8585	High Similarity	NPC229242
0.8559	High Similarity	NPC472981
0.8491	Intermediate Similarity	NPC253423
0.8468	Intermediate Similarity	NPC249811
0.844	Intermediate Similarity	NPC329556
0.844	Intermediate Similarity	NPC247976
0.8435	Intermediate Similarity	NPC93181
0.8435	Intermediate Similarity	NPC274839
0.8378	Intermediate Similarity	NPC37914
0.8374	Intermediate Similarity	NPC51448
0.8374	Intermediate Similarity	NPC115797
0.8361	Intermediate Similarity	NPC470765
0.8348	Intermediate Similarity	NPC471721
0.8348	Intermediate Similarity	NPC196673
0.8333	Intermediate Similarity	NPC369
0.8333	Intermediate Similarity	NPC293831
0.8319	Intermediate Similarity	NPC133389
0.8319	Intermediate Similarity	NPC183339
0.8319	Intermediate Similarity	NPC234337
0.8305	Intermediate Similarity	NPC328694
0.8304	Intermediate Similarity	NPC211439
0.8293	Intermediate Similarity	NPC473220
0.8293	Intermediate Similarity	NPC470753
0.8291	Intermediate Similarity	NPC212891
0.8279	Intermediate Similarity	NPC236189
0.8276	Intermediate Similarity	NPC221275
0.8264	Intermediate Similarity	NPC282577
0.8261	Intermediate Similarity	NPC93287
0.8261	Intermediate Similarity	NPC128368
0.8257	Intermediate Similarity	NPC225079
0.825	Intermediate Similarity	NPC241001
0.8224	Intermediate Similarity	NPC61944
0.822	Intermediate Similarity	NPC160199
0.8214	Intermediate Similarity	NPC100767
0.8211	Intermediate Similarity	NPC123506
0.8211	Intermediate Similarity	NPC275576
0.8198	Intermediate Similarity	NPC329282
0.8182	Intermediate Similarity	NPC284477
0.8182	Intermediate Similarity	NPC25168
0.8174	Intermediate Similarity	NPC292834
0.8167	Intermediate Similarity	NPC478121
0.816	Intermediate Similarity	NPC96024
0.8145	Intermediate Similarity	NPC169913
0.813	Intermediate Similarity	NPC199273
0.8115	Intermediate Similarity	NPC121168
0.8099	Intermediate Similarity	NPC165197
0.8095	Intermediate Similarity	NPC117899
0.8091	Intermediate Similarity	NPC282895
0.808	Intermediate Similarity	NPC84672
0.808	Intermediate Similarity	NPC72667
0.808	Intermediate Similarity	NPC78364
0.808	Intermediate Similarity	NPC176130
0.808	Intermediate Similarity	NPC69424
0.8067	Intermediate Similarity	NPC45794
0.8033	Intermediate Similarity	NPC249340
0.8033	Intermediate Similarity	NPC162935
0.8031	Intermediate Similarity	NPC108129
0.8017	Intermediate Similarity	NPC471188
0.8016	Intermediate Similarity	NPC3009
0.8016	Intermediate Similarity	NPC193203
0.8016	Intermediate Similarity	NPC229894
0.8	Intermediate Similarity	NPC253681
0.8	Intermediate Similarity	NPC254492
0.8	Intermediate Similarity	NPC474106
0.8	Intermediate Similarity	NPC228435
0.7984	Intermediate Similarity	NPC142956
0.7984	Intermediate Similarity	NPC117794
0.7969	Intermediate Similarity	NPC18798
0.7967	Intermediate Similarity	NPC297193
0.7967	Intermediate Similarity	NPC307174
0.7966	Intermediate Similarity	NPC474095
0.7966	Intermediate Similarity	NPC306740
0.7965	Intermediate Similarity	NPC172483
0.7963	Intermediate Similarity	NPC172925
0.7953	Intermediate Similarity	NPC262819
0.7953	Intermediate Similarity	NPC276238
0.7953	Intermediate Similarity	NPC303910
0.7953	Intermediate Similarity	NPC171460
0.7951	Intermediate Similarity	NPC164852
0.7949	Intermediate Similarity	NPC143768
0.7934	Intermediate Similarity	NPC42657
0.7934	Intermediate Similarity	NPC476645
0.7931	Intermediate Similarity	NPC210089
0.7931	Intermediate Similarity	NPC265513
0.7928	Intermediate Similarity	NPC469481
0.7928	Intermediate Similarity	NPC136810
0.7928	Intermediate Similarity	NPC128248
0.7928	Intermediate Similarity	NPC133809
0.7925	Intermediate Similarity	NPC62765
0.7925	Intermediate Similarity	NPC70940
0.7925	Intermediate Similarity	NPC274455
0.7925	Intermediate Similarity	NPC86670
0.792	Intermediate Similarity	NPC472592
0.7913	Intermediate Similarity	NPC85493
0.7903	Intermediate Similarity	NPC273683
0.7895	Intermediate Similarity	NPC94751
0.7895	Intermediate Similarity	NPC83409
0.7895	Intermediate Similarity	NPC185763
0.7895	Intermediate Similarity	NPC142326
0.7891	Intermediate Similarity	NPC31539
0.7886	Intermediate Similarity	NPC154696
0.7881	Intermediate Similarity	NPC153053
0.7874	Intermediate Similarity	NPC48248
0.7869	Intermediate Similarity	NPC232958
0.7863	Intermediate Similarity	NPC321852
0.7863	Intermediate Similarity	NPC280789
0.7851	Intermediate Similarity	NPC161943
0.7851	Intermediate Similarity	NPC273282
0.7851	Intermediate Similarity	NPC474890
0.784	Intermediate Similarity	NPC173978
0.7833	Intermediate Similarity	NPC105141
0.7833	Intermediate Similarity	NPC242764
0.7833	Intermediate Similarity	NPC83718
0.7829	Intermediate Similarity	NPC471851
0.7826	Intermediate Similarity	NPC472980
0.7826	Intermediate Similarity	NPC472979
0.7826	Intermediate Similarity	NPC27252
0.7823	Intermediate Similarity	NPC244351
0.7823	Intermediate Similarity	NPC283514
0.7812	Intermediate Similarity	NPC131684
0.7807	Intermediate Similarity	NPC134120
0.7807	Intermediate Similarity	NPC209632
0.7805	Intermediate Similarity	NPC178395
0.7805	Intermediate Similarity	NPC301987
0.7805	Intermediate Similarity	NPC259703
0.7805	Intermediate Similarity	NPC35856
0.7805	Intermediate Similarity	NPC159760
0.7805	Intermediate Similarity	NPC32322
0.7805	Intermediate Similarity	NPC244994
0.7805	Intermediate Similarity	NPC222876
0.7805	Intermediate Similarity	NPC272454
0.7805	Intermediate Similarity	NPC115188
0.7805	Intermediate Similarity	NPC179092
0.7805	Intermediate Similarity	NPC292665
0.7805	Intermediate Similarity	NPC26433
0.7803	Intermediate Similarity	NPC118919
0.7797	Intermediate Similarity	NPC470253
0.7797	Intermediate Similarity	NPC272524
0.7788	Intermediate Similarity	NPC274443
0.7787	Intermediate Similarity	NPC184579
0.7787	Intermediate Similarity	NPC202015
0.7787	Intermediate Similarity	NPC472708
0.7787	Intermediate Similarity	NPC233165
0.7786	Intermediate Similarity	NPC202225
0.7786	Intermediate Similarity	NPC477594
0.7778	Intermediate Similarity	NPC260818
0.7769	Intermediate Similarity	NPC228318
0.7769	Intermediate Similarity	NPC125252
0.7769	Intermediate Similarity	NPC58685
0.776	Intermediate Similarity	NPC174991
0.776	Intermediate Similarity	NPC328107
0.776	Intermediate Similarity	NPC228739
0.776	Intermediate Similarity	NPC318067
0.776	Intermediate Similarity	NPC77691
0.7757	Intermediate Similarity	NPC26224
0.7752	Intermediate Similarity	NPC72915
0.775	Intermediate Similarity	NPC322197
0.7744	Intermediate Similarity	NPC62272
0.7742	Intermediate Similarity	NPC198336
0.7742	Intermediate Similarity	NPC120545
0.7736	Intermediate Similarity	NPC329064
0.7734	Intermediate Similarity	NPC282923
0.7731	Intermediate Similarity	NPC211421
0.7731	Intermediate Similarity	NPC242136
0.7727	Intermediate Similarity	NPC161632
0.7727	Intermediate Similarity	NPC472372
0.7727	Intermediate Similarity	NPC472374
0.7727	Intermediate Similarity	NPC472551
0.7727	Intermediate Similarity	NPC477596
0.7727	Intermediate Similarity	NPC472545
0.7727	Intermediate Similarity	NPC290803
0.7724	Intermediate Similarity	NPC206778
0.7724	Intermediate Similarity	NPC473243
0.7724	Intermediate Similarity	NPC133302
0.7724	Intermediate Similarity	NPC285829
0.7719	Intermediate Similarity	NPC249067
0.7719	Intermediate Similarity	NPC114594
0.7717	Intermediate Similarity	NPC51292
0.7717	Intermediate Similarity	NPC160499
0.7717	Intermediate Similarity	NPC3224
0.7712	Intermediate Similarity	NPC186128

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 NPC186933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	900
0.2-0.3	1250
0.3-0.4	2512
0.4-0.5	2515
0.5-0.6	1247
0.6-0.7	382
0.7-0.8	84
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8929	High Similarity	NPD5951	Approved
0.8475	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1930	Approved
0.844	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1929	Approved
0.8393	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD2066	Phase 3
0.7963	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7008	Discontinued
0.7931	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1086	Approved
0.7925	Intermediate Similarity	NPD1089	Approved
0.7925	Intermediate Similarity	NPD9258	Approved
0.7925	Intermediate Similarity	NPD9256	Approved
0.7925	Intermediate Similarity	NPD1090	Approved
0.7857	Intermediate Similarity	NPD1932	Approved
0.783	Intermediate Similarity	NPD800	Approved
0.7798	Intermediate Similarity	NPD1693	Approved
0.7778	Intermediate Similarity	NPD1088	Approved
0.776	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2329	Discontinued
0.7744	Intermediate Similarity	NPD5404	Approved
0.7744	Intermediate Similarity	NPD5406	Approved
0.7744	Intermediate Similarity	NPD5408	Approved
0.7744	Intermediate Similarity	NPD5405	Approved
0.7719	Intermediate Similarity	NPD1237	Approved
0.7706	Intermediate Similarity	NPD1202	Approved
0.7698	Intermediate Similarity	NPD1283	Approved
0.7685	Intermediate Similarity	NPD1239	Approved
0.7667	Intermediate Similarity	NPD2629	Approved
0.7658	Intermediate Similarity	NPD1565	Approved
0.7658	Intermediate Similarity	NPD1566	Phase 3
0.7658	Intermediate Similarity	NPD1564	Approved
0.7647	Intermediate Similarity	NPD7003	Approved
0.7642	Intermediate Similarity	NPD1087	Approved
0.7638	Intermediate Similarity	NPD1164	Approved
0.7627	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7610	Discontinued
0.76	Intermediate Similarity	NPD1201	Approved
0.7565	Intermediate Similarity	NPD164	Approved
0.7547	Intermediate Similarity	NPD9257	Approved
0.7547	Intermediate Similarity	NPD9259	Approved
0.7545	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3495	Discontinued
0.75	Intermediate Similarity	NPD1470	Approved
0.746	Intermediate Similarity	NPD1281	Approved
0.7458	Intermediate Similarity	NPD2182	Approved
0.7442	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD2932	Approved
0.744	Intermediate Similarity	NPD3019	Approved
0.744	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD2346	Discontinued
0.7417	Intermediate Similarity	NPD9508	Approved
0.7417	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5909	Discontinued
0.7405	Intermediate Similarity	NPD6966	Discovery
0.7402	Intermediate Similarity	NPD4878	Approved
0.7398	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1317	Discontinued
0.7387	Intermediate Similarity	NPD1563	Approved
0.7368	Intermediate Similarity	NPD1238	Approved
0.736	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3764	Approved
0.7328	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6049	Phase 2
0.7321	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4626	Approved
0.7302	Intermediate Similarity	NPD2345	Approved
0.7297	Intermediate Similarity	NPD7631	Approved
0.7286	Intermediate Similarity	NPD7236	Approved
0.7281	Intermediate Similarity	NPD9495	Approved
0.728	Intermediate Similarity	NPD7009	Phase 2
0.7279	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2799	Discontinued
0.7264	Intermediate Similarity	NPD9491	Approved
0.7257	Intermediate Similarity	NPD1989	Approved
0.7236	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD9264	Approved
0.7227	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD9267	Approved
0.7227	Intermediate Similarity	NPD9263	Approved
0.7226	Intermediate Similarity	NPD2935	Discontinued
0.7213	Intermediate Similarity	NPD7635	Approved
0.7213	Intermediate Similarity	NPD5277	Phase 2
0.7207	Intermediate Similarity	NPD7609	Phase 3
0.7188	Intermediate Similarity	NPD6287	Discontinued
0.7167	Intermediate Similarity	NPD9266	Approved
0.7167	Intermediate Similarity	NPD74	Approved
0.7165	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5306	Approved
0.7165	Intermediate Similarity	NPD5305	Approved
0.7164	Intermediate Similarity	NPD7961	Discontinued
0.7164	Intermediate Similarity	NPD6663	Approved
0.7156	Intermediate Similarity	NPD650	Approved
0.7153	Intermediate Similarity	NPD7239	Suspended
0.7121	Intermediate Similarity	NPD5736	Approved
0.712	Intermediate Similarity	NPD9493	Approved
0.7103	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3971	Phase 1
0.7087	Intermediate Similarity	NPD1651	Approved
0.7087	Intermediate Similarity	NPD4105	Approved
0.7087	Intermediate Similarity	NPD4102	Approved
0.7075	Intermediate Similarity	NPD226	Approved
0.7054	Intermediate Similarity	NPD4807	Approved
0.7054	Intermediate Similarity	NPD4806	Approved
0.7045	Intermediate Similarity	NPD4980	Approved
0.7045	Intermediate Similarity	NPD2798	Approved
0.704	Intermediate Similarity	NPD4198	Discontinued
0.704	Intermediate Similarity	NPD3317	Approved
0.7034	Intermediate Similarity	NPD6647	Phase 2
0.7029	Intermediate Similarity	NPD4308	Phase 3
0.7027	Intermediate Similarity	NPD5346	Phase 2
0.7027	Intermediate Similarity	NPD5347	Phase 2
0.7018	Intermediate Similarity	NPD9260	Approved
0.7016	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6273	Approved
0.7008	Intermediate Similarity	NPD9545	Approved
0.7007	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3226	Approved
0.6986	Remote Similarity	NPD7458	Discontinued
0.6985	Remote Similarity	NPD2979	Phase 3
0.6977	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4106	Approved
0.6977	Remote Similarity	NPD3026	Approved
0.6977	Remote Similarity	NPD4136	Approved
0.6977	Remote Similarity	NPD4135	Approved
0.6977	Remote Similarity	NPD4879	Approved
0.6977	Remote Similarity	NPD3023	Approved
0.697	Remote Similarity	NPD2797	Approved
0.6963	Remote Similarity	NPD2313	Discontinued
0.6953	Remote Similarity	NPD5691	Approved
0.6953	Remote Similarity	NPD1245	Approved
0.6953	Remote Similarity	NPD3025	Approved
0.6953	Remote Similarity	NPD3024	Approved
0.6944	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2342	Discontinued
0.693	Remote Similarity	NPD845	Approved
0.6929	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3020	Approved
0.6912	Remote Similarity	NPD7714	Approved
0.6912	Remote Similarity	NPD7715	Approved
0.6906	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8166	Discontinued
0.6901	Remote Similarity	NPD4628	Phase 3
0.6897	Remote Similarity	NPD288	Approved
0.6894	Remote Similarity	NPD1888	Phase 1
0.6894	Remote Similarity	NPD1876	Approved
0.6891	Remote Similarity	NPD9261	Approved
0.6887	Remote Similarity	NPD9490	Approved
0.6875	Remote Similarity	NPD7390	Discontinued
0.6871	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1608	Approved
0.687	Remote Similarity	NPD3972	Approved
0.6847	Remote Similarity	NPD4793	Discontinued
0.6842	Remote Similarity	NPD1508	Approved
0.6831	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1246	Approved
0.6825	Remote Similarity	NPD9281	Approved
0.6818	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5157	Phase 1
0.6818	Remote Similarity	NPD5159	Phase 2
0.681	Remote Similarity	NPD844	Approved
0.6806	Remote Similarity	NPD3300	Phase 2
0.68	Remote Similarity	NPD7094	Approved
0.68	Remote Similarity	NPD6858	Approved
0.6792	Remote Similarity	NPD227	Approved
0.6792	Remote Similarity	NPD225	Approved
0.6783	Remote Similarity	NPD3750	Approved
0.6783	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1104	Approved
0.6761	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD942	Approved
0.6742	Remote Similarity	NPD9717	Approved
0.6739	Remote Similarity	NPD4307	Phase 2
0.6738	Remote Similarity	NPD2531	Phase 2
0.6738	Remote Similarity	NPD4477	Approved
0.6738	Remote Similarity	NPD4476	Approved
0.6738	Remote Similarity	NPD2438	Suspended
0.6723	Remote Similarity	NPD1616	Discontinued
0.6719	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1203	Approved
0.6715	Remote Similarity	NPD3268	Approved
0.6715	Remote Similarity	NPD411	Approved
0.6712	Remote Similarity	NPD2533	Approved
0.6712	Remote Similarity	NPD2534	Approved
0.6712	Remote Similarity	NPD2532	Approved
0.6711	Remote Similarity	NPD7057	Phase 3
0.6711	Remote Similarity	NPD7058	Phase 2
0.669	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD1843	Approved
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD5618	Discontinued

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