NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	520.38
Volume:	552.055
LogP:	3.75
LogD:	3.953
LogS:	-4.345
# Rotatable Bonds:	5
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	6.75
Fsp3:	0.935
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044
MDCK Permeability:	2.3689040972385556e-05
Pgp-inhibitor:	0.667
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.471
20% Bioavailability (F20%):	0.334
30% Bioavailability (F30%):	0.249

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	91.88103485107422%
Volume Distribution (VD):	0.97
Pgp-substrate:	4.01338529586792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.388
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.636

ADMET: Excretion

Clearance (CL):	4.843
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.241
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC476895

Natural Product ID:	NPC476895
*Common Name:**	Cordianol C
IUPAC Name:	(1R,2S,3R,5R,6S,9R,10R,13R,15S)-6-[(E)-4,5-dihydroxy-6-methoxy-6-methylhept-2-en-2-yl]-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.01,13.02,10.05,9]nonadecane-3,15-diol
Synonyms:	Cordianol C
Standard InCHIKey:	ANFJBMXRWPPYJK-AFPDNCCGSA-N
Standard InCHI:	InChI=1S/C31H52O6/c1-18(15-22(33)25(34)27(4,5)36-8)19-9-11-28(6)20(19)16-21(32)24-29(28,7)12-10-23-26(2,3)31(35)14-13-30(23,24)17-37-31/h15,19-25,32-35H,9-14,16-17H2,1-8H3/b18-15+/t19-,20-,21-,22?,23+,24+,25?,28-,29-,30-,31+/m1/s1
SMILES:	C/C(=C\C(C(C(C)(C)OC)O)O)/[C@H]1CC[C@@]2([C@@H]1C[C@H]([C@H]3[C@]2(CC[C@@H]4[C@]35CC[C@@](C4(C)C)(OC5)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21590011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO6708	Cordia multispicata	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575428]
NPO6708	Cordia multispicata	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6708	Cordia multispicata	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6708	Cordia multispicata	Species	Cordiaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	19	%	PMID[14575428]

☑ 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 NPC476895 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	238
0.1-0.2	1723
0.2-0.3	5262
0.3-0.4	12667
0.4-0.5	10289
0.5-0.6	5593
0.6-0.7	4128
0.7-0.8	2293
0.8-0.85	370
0.85-0.9	106
0.9-0.95	24
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC476893
0.9785	High Similarity	NPC476896
0.9457	High Similarity	NPC476894
0.9381	High Similarity	NPC472900
0.9381	High Similarity	NPC472898
0.9381	High Similarity	NPC472899
0.9175	High Similarity	NPC473198
0.9091	High Similarity	NPC231340
0.9082	High Similarity	NPC75608
0.9072	High Similarity	NPC136816
0.9	High Similarity	NPC472897
0.9	High Similarity	NPC472896
0.8969	High Similarity	NPC47566
0.8969	High Similarity	NPC470434
0.8969	High Similarity	NPC4831
0.8969	High Similarity	NPC309425
0.8969	High Similarity	NPC472023
0.8969	High Similarity	NPC129372
0.8969	High Similarity	NPC88000
0.8969	High Similarity	NPC160734
0.8958	High Similarity	NPC280825
0.8958	High Similarity	NPC234287
0.8911	High Similarity	NPC472901
0.8866	High Similarity	NPC473200
0.8866	High Similarity	NPC469942
0.8866	High Similarity	NPC7341
0.8788	High Similarity	NPC16520
0.8788	High Similarity	NPC157659
0.8788	High Similarity	NPC245280
0.8788	High Similarity	NPC189852
0.8788	High Similarity	NPC286969
0.8788	High Similarity	NPC31907
0.8788	High Similarity	NPC472252
0.8788	High Similarity	NPC114874
0.8788	High Similarity	NPC473020
0.8788	High Similarity	NPC155010
0.8788	High Similarity	NPC131479
0.8788	High Similarity	NPC475701
0.8788	High Similarity	NPC8039
0.8788	High Similarity	NPC213190
0.8788	High Similarity	NPC211879
0.8788	High Similarity	NPC120123
0.8776	High Similarity	NPC470054
0.875	High Similarity	NPC288970
0.875	High Similarity	NPC90583
0.8738	High Similarity	NPC473021
0.8738	High Similarity	NPC472987
0.8723	High Similarity	NPC41554
0.8723	High Similarity	NPC97404
0.8713	High Similarity	NPC33053
0.871	High Similarity	NPC470361
0.87	High Similarity	NPC474464
0.87	High Similarity	NPC470885
0.87	High Similarity	NPC187400
0.87	High Similarity	NPC273879
0.87	High Similarity	NPC93352
0.87	High Similarity	NPC165033
0.87	High Similarity	NPC221562
0.8687	High Similarity	NPC312553
0.8687	High Similarity	NPC159036
0.8687	High Similarity	NPC288694
0.8687	High Similarity	NPC470053
0.8673	High Similarity	NPC471242
0.8673	High Similarity	NPC282669
0.866	High Similarity	NPC243728
0.866	High Similarity	NPC473890
0.8654	High Similarity	NPC477050
0.8646	High Similarity	NPC30477
0.8646	High Similarity	NPC8774
0.8641	High Similarity	NPC472717
0.8617	High Similarity	NPC80561
0.8617	High Similarity	NPC329596
0.8617	High Similarity	NPC11216
0.8617	High Similarity	NPC291484
0.8617	High Similarity	NPC3345
0.8617	High Similarity	NPC204188
0.8614	High Similarity	NPC269627
0.8614	High Similarity	NPC69737
0.8614	High Similarity	NPC473199
0.8614	High Similarity	NPC160816
0.8614	High Similarity	NPC208477
0.8614	High Similarity	NPC127801
0.8614	High Similarity	NPC208594
0.8614	High Similarity	NPC474015
0.8614	High Similarity	NPC194842
0.8614	High Similarity	NPC152584
0.8602	High Similarity	NPC67872
0.8602	High Similarity	NPC474668
0.86	High Similarity	NPC16573
0.8587	High Similarity	NPC6391
0.8571	High Similarity	NPC158088
0.8571	High Similarity	NPC216260
0.8571	High Similarity	NPC5358
0.8571	High Similarity	NPC470068
0.8558	High Similarity	NPC472715
0.8557	High Similarity	NPC98457
0.8557	High Similarity	NPC472989
0.8557	High Similarity	NPC207617
0.8557	High Similarity	NPC227583
0.8557	High Similarity	NPC12103
0.8544	High Similarity	NPC128133
0.8542	High Similarity	NPC65402
0.8542	High Similarity	NPC127718
0.8529	High Similarity	NPC14946
0.8529	High Similarity	NPC190395
0.8529	High Similarity	NPC473469
0.8529	High Similarity	NPC181467
0.8529	High Similarity	NPC208650
0.8529	High Similarity	NPC63368
0.8526	High Similarity	NPC210268
0.8515	High Similarity	NPC152966
0.8515	High Similarity	NPC471111
0.8511	High Similarity	NPC477917
0.8495	Intermediate Similarity	NPC470620
0.8485	Intermediate Similarity	NPC91497
0.8485	Intermediate Similarity	NPC473790
0.8485	Intermediate Similarity	NPC64348
0.8485	Intermediate Similarity	NPC471247
0.8476	Intermediate Similarity	NPC472716
0.8476	Intermediate Similarity	NPC473567
0.8476	Intermediate Similarity	NPC216595
0.8469	Intermediate Similarity	NPC26307
0.8469	Intermediate Similarity	NPC240372
0.8469	Intermediate Similarity	NPC261807
0.8462	Intermediate Similarity	NPC103627
0.8462	Intermediate Similarity	NPC65155
0.8462	Intermediate Similarity	NPC170974
0.8462	Intermediate Similarity	NPC191439
0.8454	Intermediate Similarity	NPC473348
0.8447	Intermediate Similarity	NPC472988
0.8447	Intermediate Similarity	NPC6931
0.8447	Intermediate Similarity	NPC159005
0.8447	Intermediate Similarity	NPC220427
0.8447	Intermediate Similarity	NPC246124
0.8447	Intermediate Similarity	NPC180183
0.8447	Intermediate Similarity	NPC7213
0.8447	Intermediate Similarity	NPC235824
0.8447	Intermediate Similarity	NPC38217
0.8438	Intermediate Similarity	NPC296620
0.8431	Intermediate Similarity	NPC309448
0.8431	Intermediate Similarity	NPC242748
0.8416	Intermediate Similarity	NPC162354
0.8411	Intermediate Similarity	NPC146652
0.8404	Intermediate Similarity	NPC133588
0.84	Intermediate Similarity	NPC21568
0.84	Intermediate Similarity	NPC285231
0.84	Intermediate Similarity	NPC474022
0.84	Intermediate Similarity	NPC475617
0.84	Intermediate Similarity	NPC267510
0.8387	Intermediate Similarity	NPC261266
0.8384	Intermediate Similarity	NPC309493
0.8384	Intermediate Similarity	NPC275865
0.8381	Intermediate Similarity	NPC65034
0.8381	Intermediate Similarity	NPC208189
0.837	Intermediate Similarity	NPC15534
0.837	Intermediate Similarity	NPC185568
0.8367	Intermediate Similarity	NPC103165
0.8367	Intermediate Similarity	NPC72204
0.8367	Intermediate Similarity	NPC210717
0.8367	Intermediate Similarity	NPC471903
0.8365	Intermediate Similarity	NPC43976
0.8365	Intermediate Similarity	NPC51925
0.8365	Intermediate Similarity	NPC473318
0.8365	Intermediate Similarity	NPC14630
0.8365	Intermediate Similarity	NPC250089
0.8365	Intermediate Similarity	NPC473328
0.8365	Intermediate Similarity	NPC154085
0.8365	Intermediate Similarity	NPC28844
0.8365	Intermediate Similarity	NPC157530
0.8365	Intermediate Similarity	NPC296761
0.8365	Intermediate Similarity	NPC125361
0.8365	Intermediate Similarity	NPC302057
0.8351	Intermediate Similarity	NPC305160
0.8351	Intermediate Similarity	NPC72817
0.8351	Intermediate Similarity	NPC477927
0.835	Intermediate Similarity	NPC226642
0.835	Intermediate Similarity	NPC234160
0.8333	Intermediate Similarity	NPC275671
0.8333	Intermediate Similarity	NPC473543
0.8333	Intermediate Similarity	NPC48463
0.8333	Intermediate Similarity	NPC475365
0.8333	Intermediate Similarity	NPC302584
0.8333	Intermediate Similarity	NPC312774
0.8318	Intermediate Similarity	NPC69576
0.8318	Intermediate Similarity	NPC471633
0.8318	Intermediate Similarity	NPC84949
0.8318	Intermediate Similarity	NPC31354
0.8317	Intermediate Similarity	NPC154452
0.8317	Intermediate Similarity	NPC22634
0.8317	Intermediate Similarity	NPC272015
0.8317	Intermediate Similarity	NPC31085
0.8316	Intermediate Similarity	NPC101886
0.8316	Intermediate Similarity	NPC105495
0.8302	Intermediate Similarity	NPC231797
0.8302	Intermediate Similarity	NPC475354
0.83	Intermediate Similarity	NPC473510
0.83	Intermediate Similarity	NPC324598
0.8286	Intermediate Similarity	NPC141433
0.8283	Intermediate Similarity	NPC210337
0.8283	Intermediate Similarity	NPC76486

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 NPC476895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1865
0.2-0.3	4112
0.3-0.4	2009
0.4-0.5	519
0.5-0.6	266
0.6-0.7	148
0.7-0.8	23
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD7525	Registered
0.8105	Intermediate Similarity	NPD7524	Approved
0.8091	Intermediate Similarity	NPD7328	Approved
0.8091	Intermediate Similarity	NPD7327	Approved
0.8036	Intermediate Similarity	NPD8033	Approved
0.8018	Intermediate Similarity	NPD7516	Approved
0.7979	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7946	Intermediate Similarity	NPD8377	Approved
0.7946	Intermediate Similarity	NPD8294	Approved
0.7876	Intermediate Similarity	NPD8378	Approved
0.7876	Intermediate Similarity	NPD8335	Approved
0.7876	Intermediate Similarity	NPD8380	Approved
0.7876	Intermediate Similarity	NPD8379	Approved
0.7876	Intermediate Similarity	NPD8296	Approved
0.7872	Intermediate Similarity	NPD6695	Phase 3
0.7607	Intermediate Similarity	NPD7507	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD7503	Approved
0.7553	Intermediate Similarity	NPD6930	Phase 2
0.7553	Intermediate Similarity	NPD6931	Approved
0.7551	Intermediate Similarity	NPD7750	Discontinued
0.7551	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7447	Intermediate Similarity	NPD6929	Approved
0.7447	Intermediate Similarity	NPD7645	Phase 2
0.7417	Intermediate Similarity	NPD7319	Approved
0.7391	Intermediate Similarity	NPD6942	Approved
0.7391	Intermediate Similarity	NPD7339	Approved
0.7368	Intermediate Similarity	NPD7115	Discovery
0.7368	Intermediate Similarity	NPD7514	Phase 3
0.7312	Intermediate Similarity	NPD6933	Approved
0.7257	Intermediate Similarity	NPD8133	Approved
0.7255	Intermediate Similarity	NPD7087	Discontinued
0.7234	Intermediate Similarity	NPD6925	Approved
0.7234	Intermediate Similarity	NPD5776	Phase 2
0.7188	Intermediate Similarity	NPD7332	Phase 2
0.7172	Intermediate Similarity	NPD6893	Approved
0.717	Intermediate Similarity	NPD4225	Approved
0.7158	Intermediate Similarity	NPD7145	Approved
0.7128	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6686	Approved
0.7113	Intermediate Similarity	NPD6902	Approved
0.7097	Intermediate Similarity	NPD6926	Approved
0.7097	Intermediate Similarity	NPD6924	Approved
0.7087	Intermediate Similarity	NPD7637	Suspended
0.7053	Intermediate Similarity	NPD6932	Approved
0.7034	Intermediate Similarity	NPD6054	Approved
0.7034	Intermediate Similarity	NPD6059	Approved
0.7033	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7019	Intermediate Similarity	NPD8171	Discontinued
0.701	Intermediate Similarity	NPD6928	Phase 2
0.6972	Remote Similarity	NPD7632	Discontinued
0.6939	Remote Similarity	NPD6898	Phase 1
0.6937	Remote Similarity	NPD5739	Approved
0.6937	Remote Similarity	NPD6675	Approved
0.6937	Remote Similarity	NPD6402	Approved
0.6937	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD8034	Phase 2
0.6917	Remote Similarity	NPD6370	Approved
0.6911	Remote Similarity	NPD7736	Approved
0.6907	Remote Similarity	NPD6683	Phase 2
0.6903	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4786	Approved
0.6881	Remote Similarity	NPD4159	Approved
0.6881	Remote Similarity	NPD5344	Discontinued
0.687	Remote Similarity	NPD8297	Approved
0.687	Remote Similarity	NPD6882	Approved
0.6837	Remote Similarity	NPD7509	Discontinued
0.6833	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD6016	Approved
0.6832	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5211	Phase 2
0.6814	Remote Similarity	NPD7320	Approved
0.6814	Remote Similarity	NPD6881	Approved
0.6814	Remote Similarity	NPD6899	Approved
0.681	Remote Similarity	NPD4632	Approved
0.6804	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD7492	Approved
0.678	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6009	Approved
0.6777	Remote Similarity	NPD5988	Approved
0.6759	Remote Similarity	NPD4755	Approved
0.6754	Remote Similarity	NPD6372	Approved
0.6754	Remote Similarity	NPD6373	Approved
0.6754	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6319	Approved
0.6748	Remote Similarity	NPD6616	Approved
0.6737	Remote Similarity	NPD4785	Approved
0.6737	Remote Similarity	NPD4784	Approved
0.6731	Remote Similarity	NPD6051	Approved
0.6731	Remote Similarity	NPD5328	Approved
0.6726	Remote Similarity	NPD5701	Approved
0.6726	Remote Similarity	NPD5697	Approved
0.6721	Remote Similarity	NPD8328	Phase 3
0.6702	Remote Similarity	NPD7150	Approved
0.6702	Remote Similarity	NPD7152	Approved
0.6702	Remote Similarity	NPD7151	Approved
0.6702	Remote Similarity	NPD4243	Approved
0.67	Remote Similarity	NPD3667	Approved
0.6698	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD6883	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6696	Remote Similarity	NPD7290	Approved
0.6696	Remote Similarity	NPD7102	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD6923	Approved
0.6667	Remote Similarity	NPD3168	Discontinued
0.6667	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6638	Remote Similarity	NPD6650	Approved
0.6638	Remote Similarity	NPD8130	Phase 1
0.6638	Remote Similarity	NPD6617	Approved
0.6638	Remote Similarity	NPD6869	Approved
0.6638	Remote Similarity	NPD6649	Approved
0.6638	Remote Similarity	NPD6847	Approved
0.6637	Remote Similarity	NPD6640	Phase 3
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6609	Remote Similarity	NPD6012	Approved
0.6609	Remote Similarity	NPD6014	Approved
0.6609	Remote Similarity	NPD6013	Approved
0.6606	Remote Similarity	NPD6083	Phase 2
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD7902	Approved
0.6604	Remote Similarity	NPD6079	Approved
0.6604	Remote Similarity	NPD7515	Phase 2
0.6602	Remote Similarity	NPD3618	Phase 1
0.6596	Remote Similarity	NPD7144	Approved
0.6596	Remote Similarity	NPD7143	Approved
0.6562	Remote Similarity	NPD8449	Approved
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8516	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6011	Approved
0.6518	Remote Similarity	NPD5224	Approved
0.6518	Remote Similarity	NPD5225	Approved
0.6518	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4633	Approved
0.6512	Remote Similarity	NPD8450	Suspended
0.6508	Remote Similarity	NPD6033	Approved
0.6496	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD8264	Approved
0.6491	Remote Similarity	NPD6008	Approved
0.6486	Remote Similarity	NPD6648	Approved
0.646	Remote Similarity	NPD5175	Approved
0.646	Remote Similarity	NPD5174	Approved
0.6452	Remote Similarity	NPD6067	Discontinued
0.6452	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD7625	Phase 1
0.6423	Remote Similarity	NPD5983	Phase 2
0.6415	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6355	Remote Similarity	NPD7136	Phase 2
0.6349	Remote Similarity	NPD6336	Discontinued
0.6348	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD4767	Approved
0.6341	Remote Similarity	NPD7741	Discontinued
0.633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7900	Approved
0.6327	Remote Similarity	NPD4190	Phase 3
0.6327	Remote Similarity	NPD5275	Approved
0.6321	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4754	Approved
0.6306	Remote Similarity	NPD5173	Approved
0.6303	Remote Similarity	NPD6053	Discontinued
0.63	Remote Similarity	NPD6114	Approved
0.63	Remote Similarity	NPD6115	Approved
0.63	Remote Similarity	NPD6118	Approved
0.63	Remote Similarity	NPD6697	Approved
0.6281	Remote Similarity	NPD6274	Approved
0.6273	Remote Similarity	NPD5695	Phase 3
0.626	Remote Similarity	NPD7101	Approved
0.626	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3133	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD4729	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