NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	506.36
Volume:	534.759
LogP:	3.209
LogD:	3.623
LogS:	-3.526
# Rotatable Bonds:	4
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	6.685
Fsp3:	0.933
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:	-5.036
MDCK Permeability:	2.7372832846594974e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.959
Human Intestinal Absorption (HIA):	0.599
20% Bioavailability (F20%):	0.317
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.282
Plasma Protein Binding (PPB):	90.3993911743164%
Volume Distribution (VD):	0.909
Pgp-substrate:	4.186567783355713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.875
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.517
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	2.989
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.153
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.715

Download Data

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

Natural Product: NPC476893

Natural Product ID:	NPC476893
*Common Name:**	Cordianol A
IUPAC Name:	(E)-6-[(1R,2S,3R,5R,6S,9R,10R,13R,15S)-3,15-dihydroxy-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.01,13.02,10.05,9]nonadecan-6-yl]-2-methylhept-5-ene-2,3,4-triol
Synonyms:
Standard InCHIKey:	CYPWUGDZIQZKDA-ILZSHFBESA-N
Standard InCHI:	InChI=1S/C30H50O6/c1-17(14-21(32)24(33)26(4,5)34)18-8-10-27(6)19(18)15-20(31)23-28(27,7)11-9-22-25(2,3)30(35)13-12-29(22,23)16-36-30/h14,18-24,31-35H,8-13,15-16H2,1-7H3/b17-14+/t18-,19-,20-,21?,22+,23+,24?,27-,28-,29-,30+/m1/s1
SMILES:	C/C(=C\C(C(C(C)(C)O)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:	21590009
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	=	-2.09	%	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 NPC476893 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	229
0.1-0.2	1734
0.2-0.3	5226
0.3-0.4	13074
0.4-0.5	10037
0.5-0.6	5480
0.6-0.7	4140
0.7-0.8	2325
0.8-0.85	339
0.85-0.9	102
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC476895
0.9677	High Similarity	NPC476896
0.956	High Similarity	NPC476894
0.9278	High Similarity	NPC472899
0.9278	High Similarity	NPC472900
0.9278	High Similarity	NPC472898
0.9072	High Similarity	NPC473198
0.899	High Similarity	NPC231340
0.898	High Similarity	NPC75608
0.8969	High Similarity	NPC136816
0.89	High Similarity	NPC472896
0.89	High Similarity	NPC472897
0.8866	High Similarity	NPC47566
0.8866	High Similarity	NPC4831
0.8866	High Similarity	NPC309425
0.8866	High Similarity	NPC470434
0.8866	High Similarity	NPC129372
0.8866	High Similarity	NPC160734
0.8866	High Similarity	NPC88000
0.8866	High Similarity	NPC472023
0.8854	High Similarity	NPC234287
0.8854	High Similarity	NPC280825
0.8817	High Similarity	NPC97404
0.8817	High Similarity	NPC41554
0.8812	High Similarity	NPC472901
0.8804	High Similarity	NPC470361
0.8763	High Similarity	NPC7341
0.8763	High Similarity	NPC473200
0.8763	High Similarity	NPC469942
0.871	High Similarity	NPC329596
0.871	High Similarity	NPC204188
0.871	High Similarity	NPC3345
0.871	High Similarity	NPC80561
0.871	High Similarity	NPC291484
0.871	High Similarity	NPC11216
0.8696	High Similarity	NPC67872
0.8696	High Similarity	NPC474668
0.8687	High Similarity	NPC155010
0.8687	High Similarity	NPC473020
0.8687	High Similarity	NPC475701
0.8687	High Similarity	NPC157659
0.8687	High Similarity	NPC213190
0.8687	High Similarity	NPC114874
0.8687	High Similarity	NPC131479
0.8687	High Similarity	NPC211879
0.8687	High Similarity	NPC120123
0.8687	High Similarity	NPC286969
0.8687	High Similarity	NPC8039
0.8687	High Similarity	NPC31907
0.8687	High Similarity	NPC472252
0.8687	High Similarity	NPC245280
0.8687	High Similarity	NPC189852
0.8687	High Similarity	NPC16520
0.8681	High Similarity	NPC6391
0.8673	High Similarity	NPC470054
0.8646	High Similarity	NPC288970
0.8646	High Similarity	NPC90583
0.8641	High Similarity	NPC472987
0.8641	High Similarity	NPC473021
0.8614	High Similarity	NPC33053
0.86	High Similarity	NPC474464
0.86	High Similarity	NPC470885
0.86	High Similarity	NPC187400
0.86	High Similarity	NPC273879
0.86	High Similarity	NPC93352
0.86	High Similarity	NPC165033
0.86	High Similarity	NPC221562
0.8587	High Similarity	NPC470620
0.8586	High Similarity	NPC312553
0.8586	High Similarity	NPC159036
0.8586	High Similarity	NPC288694
0.8586	High Similarity	NPC470053
0.8571	High Similarity	NPC471242
0.8571	High Similarity	NPC282669
0.8558	High Similarity	NPC477050
0.8557	High Similarity	NPC243728
0.8557	High Similarity	NPC473890
0.8544	High Similarity	NPC472717
0.8542	High Similarity	NPC8774
0.8542	High Similarity	NPC30477
0.8515	High Similarity	NPC269627
0.8515	High Similarity	NPC194842
0.8515	High Similarity	NPC208477
0.8515	High Similarity	NPC473199
0.8515	High Similarity	NPC69737
0.8515	High Similarity	NPC474015
0.8515	High Similarity	NPC160816
0.8515	High Similarity	NPC152584
0.8515	High Similarity	NPC208594
0.8515	High Similarity	NPC127801
0.85	High Similarity	NPC16573
0.8495	Intermediate Similarity	NPC133588
0.8485	Intermediate Similarity	NPC474022
0.8478	Intermediate Similarity	NPC261266
0.8469	Intermediate Similarity	NPC5358
0.8469	Intermediate Similarity	NPC216260
0.8469	Intermediate Similarity	NPC158088
0.8469	Intermediate Similarity	NPC470068
0.8462	Intermediate Similarity	NPC472715
0.8462	Intermediate Similarity	NPC185568
0.8454	Intermediate Similarity	NPC98457
0.8454	Intermediate Similarity	NPC471903
0.8454	Intermediate Similarity	NPC472989
0.8454	Intermediate Similarity	NPC227583
0.8454	Intermediate Similarity	NPC207617
0.8454	Intermediate Similarity	NPC12103
0.8454	Intermediate Similarity	NPC72204
0.8447	Intermediate Similarity	NPC128133
0.8438	Intermediate Similarity	NPC65402
0.8438	Intermediate Similarity	NPC127718
0.8431	Intermediate Similarity	NPC63368
0.8431	Intermediate Similarity	NPC473469
0.8431	Intermediate Similarity	NPC190395
0.8431	Intermediate Similarity	NPC14946
0.8431	Intermediate Similarity	NPC208650
0.8431	Intermediate Similarity	NPC181467
0.8421	Intermediate Similarity	NPC210268
0.8421	Intermediate Similarity	NPC275671
0.8416	Intermediate Similarity	NPC471111
0.8416	Intermediate Similarity	NPC152966
0.8404	Intermediate Similarity	NPC101886
0.8404	Intermediate Similarity	NPC477917
0.8404	Intermediate Similarity	NPC105495
0.8384	Intermediate Similarity	NPC473790
0.8384	Intermediate Similarity	NPC471247
0.8384	Intermediate Similarity	NPC64348
0.8384	Intermediate Similarity	NPC91497
0.8381	Intermediate Similarity	NPC473567
0.8381	Intermediate Similarity	NPC472716
0.8381	Intermediate Similarity	NPC216595
0.8367	Intermediate Similarity	NPC26307
0.8367	Intermediate Similarity	NPC261807
0.8367	Intermediate Similarity	NPC240372
0.8367	Intermediate Similarity	NPC177818
0.8365	Intermediate Similarity	NPC191439
0.8365	Intermediate Similarity	NPC170974
0.8365	Intermediate Similarity	NPC65155
0.8365	Intermediate Similarity	NPC103627
0.8352	Intermediate Similarity	NPC474634
0.8352	Intermediate Similarity	NPC207013
0.8351	Intermediate Similarity	NPC477969
0.8351	Intermediate Similarity	NPC135224
0.8351	Intermediate Similarity	NPC473348
0.835	Intermediate Similarity	NPC159005
0.835	Intermediate Similarity	NPC235824
0.835	Intermediate Similarity	NPC246124
0.835	Intermediate Similarity	NPC220427
0.835	Intermediate Similarity	NPC38217
0.835	Intermediate Similarity	NPC6931
0.835	Intermediate Similarity	NPC7213
0.835	Intermediate Similarity	NPC180183
0.835	Intermediate Similarity	NPC472988
0.8333	Intermediate Similarity	NPC309448
0.8333	Intermediate Similarity	NPC296620
0.8333	Intermediate Similarity	NPC242748
0.8333	Intermediate Similarity	NPC310013
0.8318	Intermediate Similarity	NPC146652
0.8317	Intermediate Similarity	NPC162354
0.8316	Intermediate Similarity	NPC14380
0.8316	Intermediate Similarity	NPC295668
0.8316	Intermediate Similarity	NPC245410
0.8316	Intermediate Similarity	NPC475751
0.8316	Intermediate Similarity	NPC470390
0.8316	Intermediate Similarity	NPC473956
0.8316	Intermediate Similarity	NPC192437
0.8316	Intermediate Similarity	NPC270511
0.83	Intermediate Similarity	NPC21568
0.83	Intermediate Similarity	NPC475617
0.83	Intermediate Similarity	NPC285231
0.83	Intermediate Similarity	NPC176406
0.83	Intermediate Similarity	NPC267510
0.8298	Intermediate Similarity	NPC475605
0.8298	Intermediate Similarity	NPC4574
0.8298	Intermediate Similarity	NPC475664
0.8298	Intermediate Similarity	NPC212596
0.8286	Intermediate Similarity	NPC65034
0.8286	Intermediate Similarity	NPC208189
0.8283	Intermediate Similarity	NPC275865
0.8283	Intermediate Similarity	NPC309493
0.828	Intermediate Similarity	NPC293287
0.828	Intermediate Similarity	NPC299068
0.828	Intermediate Similarity	NPC139724
0.828	Intermediate Similarity	NPC201273
0.828	Intermediate Similarity	NPC24277
0.828	Intermediate Similarity	NPC152808
0.8269	Intermediate Similarity	NPC125361
0.8269	Intermediate Similarity	NPC51925
0.8269	Intermediate Similarity	NPC250089
0.8269	Intermediate Similarity	NPC473328
0.8269	Intermediate Similarity	NPC154085
0.8269	Intermediate Similarity	NPC473318
0.8269	Intermediate Similarity	NPC157530
0.8269	Intermediate Similarity	NPC14630
0.8269	Intermediate Similarity	NPC296761
0.8269	Intermediate Similarity	NPC28844
0.8269	Intermediate Similarity	NPC302057
0.8269	Intermediate Similarity	NPC43976
0.8265	Intermediate Similarity	NPC210717
0.8265	Intermediate Similarity	NPC103165
0.8261	Intermediate Similarity	NPC15534

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 NPC476893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1855
0.2-0.3	4108
0.3-0.4	2027
0.4-0.5	521
0.5-0.6	254
0.6-0.7	157
0.7-0.8	22
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
0.8222	Intermediate Similarity	NPD7525	Registered
0.8065	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7328	Approved
0.8	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD7524	Approved
0.7957	Intermediate Similarity	NPD6695	Phase 3
0.7946	Intermediate Similarity	NPD8033	Approved
0.7928	Intermediate Similarity	NPD7516	Approved
0.7857	Intermediate Similarity	NPD8294	Approved
0.7857	Intermediate Similarity	NPD8377	Approved
0.7788	Intermediate Similarity	NPD8380	Approved
0.7788	Intermediate Similarity	NPD8296	Approved
0.7788	Intermediate Similarity	NPD8379	Approved
0.7788	Intermediate Similarity	NPD8335	Approved
0.7788	Intermediate Similarity	NPD8378	Approved
0.767	Intermediate Similarity	NPD7640	Approved
0.767	Intermediate Similarity	NPD7639	Approved
0.7634	Intermediate Similarity	NPD6930	Phase 2
0.7634	Intermediate Similarity	NPD6931	Approved
0.7629	Intermediate Similarity	NPD7750	Discontinued
0.7629	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7638	Approved
0.7527	Intermediate Similarity	NPD6929	Approved
0.7527	Intermediate Similarity	NPD7645	Phase 2
0.7521	Intermediate Similarity	NPD7507	Approved
0.7478	Intermediate Similarity	NPD7503	Approved
0.7473	Intermediate Similarity	NPD6942	Approved
0.7473	Intermediate Similarity	NPD7339	Approved
0.7447	Intermediate Similarity	NPD7514	Phase 3
0.7407	Intermediate Similarity	NPD6412	Phase 2
0.7391	Intermediate Similarity	NPD6933	Approved
0.7333	Intermediate Similarity	NPD7319	Approved
0.7327	Intermediate Similarity	NPD7087	Discontinued
0.7312	Intermediate Similarity	NPD5776	Phase 2
0.7312	Intermediate Similarity	NPD6925	Approved
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7263	Intermediate Similarity	NPD7332	Phase 2
0.7245	Intermediate Similarity	NPD6893	Approved
0.7234	Intermediate Similarity	NPD7145	Approved
0.7204	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6902	Approved
0.7174	Intermediate Similarity	NPD6926	Approved
0.7174	Intermediate Similarity	NPD6924	Approved
0.7168	Intermediate Similarity	NPD8133	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7128	Intermediate Similarity	NPD6932	Approved
0.7111	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6399	Phase 3
0.7083	Intermediate Similarity	NPD6928	Phase 2
0.7075	Intermediate Similarity	NPD4225	Approved
0.7037	Intermediate Similarity	NPD7632	Discontinued
0.7027	Intermediate Similarity	NPD6686	Approved
0.701	Intermediate Similarity	NPD6898	Phase 1
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD8034	Phase 2
0.699	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD6683	Phase 2
0.697	Remote Similarity	NPD4786	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.693	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD8171	Discontinued
0.6907	Remote Similarity	NPD7509	Discontinued
0.69	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5211	Phase 2
0.6875	Remote Similarity	NPD6881	Approved
0.6875	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6822	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD6372	Approved
0.6814	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6373	Approved
0.6809	Remote Similarity	NPD4785	Approved
0.6809	Remote Similarity	NPD4784	Approved
0.6796	Remote Similarity	NPD5328	Approved
0.6796	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD5344	Discontinued
0.6789	Remote Similarity	NPD4159	Approved
0.6786	Remote Similarity	NPD5697	Approved
0.6786	Remote Similarity	NPD5701	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6774	Remote Similarity	NPD4243	Approved
0.6768	Remote Similarity	NPD3667	Approved
0.6762	Remote Similarity	NPD4202	Approved
0.6757	Remote Similarity	NPD5141	Approved
0.6754	Remote Similarity	NPD6883	Approved
0.6754	Remote Similarity	NPD4634	Approved
0.6754	Remote Similarity	NPD7290	Approved
0.6754	Remote Similarity	NPD7102	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6016	Approved
0.6739	Remote Similarity	NPD6922	Approved
0.6739	Remote Similarity	NPD6923	Approved
0.6735	Remote Similarity	NPD4748	Discontinued
0.6724	Remote Similarity	NPD4632	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.6698	Remote Similarity	NPD7748	Approved
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD4700	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6847	Approved
0.6696	Remote Similarity	NPD8130	Phase 1
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6617	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD8328	Phase 3
0.6613	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD8293	Discontinued
0.6579	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD3168	Discontinued
0.6562	Remote Similarity	NPD8264	Approved
0.6552	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6640	Phase 3
0.6549	Remote Similarity	NPD6008	Approved
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5223	Approved
0.6484	Remote Similarity	NPD8449	Approved
0.6476	Remote Similarity	NPD4753	Phase 2
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8450	Suspended
0.6429	Remote Similarity	NPD6033	Approved
0.6422	Remote Similarity	NPD4697	Phase 3
0.6422	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5221	Approved
0.6422	Remote Similarity	NPD5222	Approved
0.6415	Remote Similarity	NPD7136	Phase 2
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4768	Approved
0.6404	Remote Similarity	NPD4767	Approved
0.6396	Remote Similarity	NPD6648	Approved
0.6393	Remote Similarity	NPD7741	Discontinued
0.6392	Remote Similarity	NPD5275	Approved
0.6392	Remote Similarity	NPD4190	Phase 3
0.6389	Remote Similarity	NPD7900	Approved
0.6389	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4754	Approved
0.6371	Remote Similarity	NPD6067	Discontinued
0.6371	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD6697	Approved
0.6364	Remote Similarity	NPD5173	Approved
0.6364	Remote Similarity	NPD6118	Approved
0.6364	Remote Similarity	NPD6114	Approved
0.6364	Remote Similarity	NPD6115	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.635	Remote Similarity	NPD7625	Phase 1
0.6341	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD6274	Approved
0.633	Remote Similarity	NPD5695	Phase 3
0.6325	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3668	Phase 3
0.6311	Remote Similarity	NPD7101	Approved
0.6311	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3133	Approved
0.6311	Remote Similarity	NPD7100	Approved
0.6311	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD5696	Approved
0.63	Remote Similarity	NPD4195	Approved
0.6296	Remote Similarity	NPD5778	Approved
0.6296	Remote Similarity	NPD5779	Approved
0.6293	Remote Similarity	NPD5128	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