NPASS Compound

Structure

NPC474602 OpenBabel07101718192D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 13 20 1 1 0 0 0 14 16 1 0 0 0 0 14 22 1 1 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 1 0 0 0 19 24 1 0 0 0 0 20 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.15
Volume:	369.188
LogP:	3.468
LogD:	3.766
LogS:	-4.609
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.696
Synthetic Accessibility Score:	5.178
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.557
MDCK Permeability:	2.6857713237404823e-05
Pgp-inhibitor:	0.741
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	93.45801544189453%
Volume Distribution (VD):	1.449
Pgp-substrate:	5.508136749267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.321
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.818
CYP3A4-substrate:	0.651

ADMET: Excretion

Clearance (CL):	5.828
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.368
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.236
Skin Sensitization:	0.931
Carcinogencity:	0.893
Eye Corrosion:	0.257
Eye Irritation:	0.09
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC474602

Natural Product ID:	NPC474602
*Common Name:**	1S-Hydroxy-1,2-Dihydrosphaerococcenol-A
IUPAC Name:	(4R,4aS,4bS,5S,8S,8aS,10aR)-8a-(bromomethyl)-4,5-dihydroxy-4,10a-dimethyl-8-propan-2-yl-4a,4b,5,6,7,8,9,10-octahydrophenanthren-3-one
Synonyms:
Standard InCHIKey:	REIJBRJPDFHYHQ-IAUSHHJMSA-N
Standard InCHI:	InChI=1S/C20H31BrO3/c1-12(2)13-5-6-14(22)16-17-18(3,9-10-20(13,16)11-21)8-7-15(23)19(17,4)24/h7-8,12-14,16-17,22,24H,5-6,9-11H2,1-4H3/t13-,14-,16-,17-,18-,19-,20-/m0/s1
SMILES:	BrC[C@@]12CC[C@]3([C@H]([C@@H]2[C@H](CC[C@H]1C(C)C)O)[C@@](C)(O)C(=O)C=C3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476561
PubChem CID:	44578744
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520219]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18597527]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20045651]
NPO29354	Sphaerococcus coronopifolius	Species	Sphaerococcaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug.mL-1	PMID[461151]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[461151]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.25	ug.mL-1	PMID[461151]

☑ 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 NPC474602 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	206
0.1-0.2	1384
0.2-0.3	5785
0.3-0.4	12965
0.4-0.5	10753
0.5-0.6	6636
0.6-0.7	4094
0.7-0.8	842
0.8-0.85	30
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8556	High Similarity	NPC33663
0.8404	Intermediate Similarity	NPC99380
0.84	Intermediate Similarity	NPC133921
0.8367	Intermediate Similarity	NPC144956
0.828	Intermediate Similarity	NPC158778
0.8261	Intermediate Similarity	NPC94666
0.8211	Intermediate Similarity	NPC185936
0.8211	Intermediate Similarity	NPC168027
0.8202	Intermediate Similarity	NPC469637
0.8191	Intermediate Similarity	NPC472973
0.8163	Intermediate Similarity	NPC18509
0.8132	Intermediate Similarity	NPC64600
0.8085	Intermediate Similarity	NPC328539
0.8085	Intermediate Similarity	NPC471791
0.8085	Intermediate Similarity	NPC471793
0.8041	Intermediate Similarity	NPC472977
0.8041	Intermediate Similarity	NPC471207
0.8041	Intermediate Similarity	NPC478089
0.8041	Intermediate Similarity	NPC472976
0.8041	Intermediate Similarity	NPC23170
0.8022	Intermediate Similarity	NPC48362
0.8021	Intermediate Similarity	NPC472978
0.8021	Intermediate Similarity	NPC472975
0.8	Intermediate Similarity	NPC119416
0.8	Intermediate Similarity	NPC329643
0.8	Intermediate Similarity	NPC476809
0.7979	Intermediate Similarity	NPC298904
0.7979	Intermediate Similarity	NPC109900
0.7979	Intermediate Similarity	NPC472324
0.7959	Intermediate Similarity	NPC473170
0.7957	Intermediate Similarity	NPC476426
0.7938	Intermediate Similarity	NPC477435
0.7938	Intermediate Similarity	NPC477436
0.7921	Intermediate Similarity	NPC470184
0.7917	Intermediate Similarity	NPC474209
0.7917	Intermediate Similarity	NPC475823
0.79	Intermediate Similarity	NPC114274
0.7895	Intermediate Similarity	NPC230387
0.7895	Intermediate Similarity	NPC206060
0.7895	Intermediate Similarity	NPC474925
0.7895	Intermediate Similarity	NPC474677
0.7885	Intermediate Similarity	NPC44063
0.7879	Intermediate Similarity	NPC192428
0.7872	Intermediate Similarity	NPC34190
0.7872	Intermediate Similarity	NPC327115
0.7872	Intermediate Similarity	NPC20688
0.7872	Intermediate Similarity	NPC472974
0.7857	Intermediate Similarity	NPC245972
0.7857	Intermediate Similarity	NPC212812
0.7857	Intermediate Similarity	NPC474328
0.7857	Intermediate Similarity	NPC103527
0.7857	Intermediate Similarity	NPC196485
0.7857	Intermediate Similarity	NPC160413
0.7849	Intermediate Similarity	NPC40687
0.7849	Intermediate Similarity	NPC251170
0.7835	Intermediate Similarity	NPC248913
0.7835	Intermediate Similarity	NPC272746
0.7835	Intermediate Similarity	NPC26865
0.7822	Intermediate Similarity	NPC472972
0.7822	Intermediate Similarity	NPC46761
0.7812	Intermediate Similarity	NPC275740
0.7812	Intermediate Similarity	NPC86319
0.7812	Intermediate Similarity	NPC474245
0.7802	Intermediate Similarity	NPC2482
0.78	Intermediate Similarity	NPC273269
0.7789	Intermediate Similarity	NPC58063
0.7789	Intermediate Similarity	NPC471792
0.7789	Intermediate Similarity	NPC475740
0.7778	Intermediate Similarity	NPC476808
0.7778	Intermediate Similarity	NPC477438
0.7778	Intermediate Similarity	NPC280725
0.7778	Intermediate Similarity	NPC139570
0.7778	Intermediate Similarity	NPC272617
0.7778	Intermediate Similarity	NPC477437
0.7778	Intermediate Similarity	NPC259286
0.7767	Intermediate Similarity	NPC311612
0.7766	Intermediate Similarity	NPC469993
0.7766	Intermediate Similarity	NPC470574
0.7766	Intermediate Similarity	NPC197823
0.7755	Intermediate Similarity	NPC12722
0.7755	Intermediate Similarity	NPC134826
0.7755	Intermediate Similarity	NPC211230
0.7736	Intermediate Similarity	NPC214644
0.7736	Intermediate Similarity	NPC2766
0.7732	Intermediate Similarity	NPC128672
0.7732	Intermediate Similarity	NPC472325
0.7732	Intermediate Similarity	NPC85173
0.7732	Intermediate Similarity	NPC134321
0.7717	Intermediate Similarity	NPC121984
0.7717	Intermediate Similarity	NPC119229
0.7717	Intermediate Similarity	NPC14151
0.7717	Intermediate Similarity	NPC473217
0.7714	Intermediate Similarity	NPC185
0.7708	Intermediate Similarity	NPC131470
0.7708	Intermediate Similarity	NPC53911
0.7708	Intermediate Similarity	NPC471722
0.7708	Intermediate Similarity	NPC143767
0.7708	Intermediate Similarity	NPC472802
0.77	Intermediate Similarity	NPC96859
0.77	Intermediate Similarity	NPC469545
0.77	Intermediate Similarity	NPC157113
0.77	Intermediate Similarity	NPC61369
0.77	Intermediate Similarity	NPC328162
0.77	Intermediate Similarity	NPC305483
0.77	Intermediate Similarity	NPC62516
0.77	Intermediate Similarity	NPC249954
0.77	Intermediate Similarity	NPC5532
0.77	Intermediate Similarity	NPC473158
0.7685	Intermediate Similarity	NPC90769
0.7684	Intermediate Similarity	NPC158393
0.7684	Intermediate Similarity	NPC474732
0.7684	Intermediate Similarity	NPC145879
0.7684	Intermediate Similarity	NPC474778
0.7684	Intermediate Similarity	NPC472986
0.7684	Intermediate Similarity	NPC31564
0.7684	Intermediate Similarity	NPC179591
0.7684	Intermediate Similarity	NPC472985
0.7684	Intermediate Similarity	NPC474733
0.7684	Intermediate Similarity	NPC51014
0.7677	Intermediate Similarity	NPC293086
0.7677	Intermediate Similarity	NPC477439
0.7677	Intermediate Similarity	NPC196227
0.767	Intermediate Similarity	NPC87351
0.7667	Intermediate Similarity	NPC197659
0.7667	Intermediate Similarity	NPC472746
0.7664	Intermediate Similarity	NPC235077
0.766	Intermediate Similarity	NPC476412
0.766	Intermediate Similarity	NPC470812
0.766	Intermediate Similarity	NPC237712
0.7653	Intermediate Similarity	NPC475806
0.7653	Intermediate Similarity	NPC131872
0.7647	Intermediate Similarity	NPC112167
0.7647	Intermediate Similarity	NPC15390
0.7634	Intermediate Similarity	NPC151519
0.7634	Intermediate Similarity	NPC103486
0.7634	Intermediate Similarity	NPC73882
0.7629	Intermediate Similarity	NPC186688
0.7629	Intermediate Similarity	NPC76879
0.7629	Intermediate Similarity	NPC31985
0.7629	Intermediate Similarity	NPC472983
0.7629	Intermediate Similarity	NPC1015
0.7629	Intermediate Similarity	NPC69627
0.7624	Intermediate Similarity	NPC38530
0.7624	Intermediate Similarity	NPC473456
0.7624	Intermediate Similarity	NPC84335
0.7624	Intermediate Similarity	NPC108078
0.7609	Intermediate Similarity	NPC108955
0.7604	Intermediate Similarity	NPC141292
0.7604	Intermediate Similarity	NPC73064
0.76	Intermediate Similarity	NPC476245
0.7596	Intermediate Similarity	NPC264048
0.7596	Intermediate Similarity	NPC179208
0.7596	Intermediate Similarity	NPC275583
0.7596	Intermediate Similarity	NPC247957
0.7596	Intermediate Similarity	NPC249187
0.7596	Intermediate Similarity	NPC131366
0.7579	Intermediate Similarity	NPC133954
0.7579	Intermediate Similarity	NPC241512
0.7579	Intermediate Similarity	NPC469948
0.7579	Intermediate Similarity	NPC79573
0.7579	Intermediate Similarity	NPC36350
0.7579	Intermediate Similarity	NPC32037
0.7579	Intermediate Similarity	NPC6185
0.7579	Intermediate Similarity	NPC474680
0.7576	Intermediate Similarity	NPC474807
0.7576	Intermediate Similarity	NPC79117
0.7576	Intermediate Similarity	NPC475255
0.7576	Intermediate Similarity	NPC109305
0.7576	Intermediate Similarity	NPC69454
0.7573	Intermediate Similarity	NPC163372
0.7573	Intermediate Similarity	NPC302537
0.7573	Intermediate Similarity	NPC81530
0.7573	Intermediate Similarity	NPC472637
0.757	Intermediate Similarity	NPC41405
0.7553	Intermediate Similarity	NPC105803
0.7551	Intermediate Similarity	NPC126993
0.7551	Intermediate Similarity	NPC223093
0.7551	Intermediate Similarity	NPC48010
0.7551	Intermediate Similarity	NPC191684
0.7551	Intermediate Similarity	NPC183283
0.7547	Intermediate Similarity	NPC3316
0.7547	Intermediate Similarity	NPC475294
0.7547	Intermediate Similarity	NPC144854
0.7528	Intermediate Similarity	NPC22134
0.7527	Intermediate Similarity	NPC55869
0.7527	Intermediate Similarity	NPC473420
0.7527	Intermediate Similarity	NPC328264
0.7526	Intermediate Similarity	NPC473229
0.7526	Intermediate Similarity	NPC310752
0.7526	Intermediate Similarity	NPC292491
0.7526	Intermediate Similarity	NPC58271
0.7525	Intermediate Similarity	NPC471463
0.7525	Intermediate Similarity	NPC477853
0.7524	Intermediate Similarity	NPC213366
0.7524	Intermediate Similarity	NPC235889
0.7524	Intermediate Similarity	NPC40170
0.7524	Intermediate Similarity	NPC284865
0.7524	Intermediate Similarity	NPC137657
0.7523	Intermediate Similarity	NPC71348
0.75	Intermediate Similarity	NPC111015

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 NPC474602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1896
0.2-0.3	4098
0.3-0.4	2012
0.4-0.5	561
0.5-0.6	170
0.6-0.7	123
0.7-0.8	84
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD5286	Approved
0.8367	Intermediate Similarity	NPD4696	Approved
0.8367	Intermediate Similarity	NPD5285	Approved
0.8283	Intermediate Similarity	NPD5223	Approved
0.8247	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD5222	Approved
0.8247	Intermediate Similarity	NPD5221	Approved
0.8211	Intermediate Similarity	NPD6079	Approved
0.82	Intermediate Similarity	NPD4633	Approved
0.82	Intermediate Similarity	NPD5225	Approved
0.82	Intermediate Similarity	NPD5224	Approved
0.82	Intermediate Similarity	NPD5211	Phase 2
0.82	Intermediate Similarity	NPD5226	Approved
0.8163	Intermediate Similarity	NPD4755	Approved
0.8163	Intermediate Similarity	NPD5173	Approved
0.8119	Intermediate Similarity	NPD5174	Approved
0.8119	Intermediate Similarity	NPD5175	Approved
0.8039	Intermediate Similarity	NPD5141	Approved
0.8	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.7885	Intermediate Similarity	NPD5697	Approved
0.7879	Intermediate Similarity	NPD4697	Phase 3
0.7872	Intermediate Similarity	NPD3618	Phase 1
0.781	Intermediate Similarity	NPD6881	Approved
0.781	Intermediate Similarity	NPD4729	Approved
0.781	Intermediate Similarity	NPD6899	Approved
0.781	Intermediate Similarity	NPD6011	Approved
0.781	Intermediate Similarity	NPD4730	Approved
0.7798	Intermediate Similarity	NPD6274	Approved
0.7767	Intermediate Similarity	NPD4754	Approved
0.7755	Intermediate Similarity	NPD4202	Approved
0.7736	Intermediate Similarity	NPD6014	Approved
0.7736	Intermediate Similarity	NPD6013	Approved
0.7736	Intermediate Similarity	NPD6012	Approved
0.7664	Intermediate Similarity	NPD5251	Approved
0.7664	Intermediate Similarity	NPD5249	Phase 3
0.7664	Intermediate Similarity	NPD7102	Approved
0.7664	Intermediate Similarity	NPD4634	Approved
0.7664	Intermediate Similarity	NPD5135	Approved
0.7664	Intermediate Similarity	NPD5169	Approved
0.7664	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5248	Approved
0.7664	Intermediate Similarity	NPD5247	Approved
0.7664	Intermediate Similarity	NPD6883	Approved
0.7664	Intermediate Similarity	NPD5250	Approved
0.7664	Intermediate Similarity	NPD7290	Approved
0.7642	Intermediate Similarity	NPD5128	Approved
0.7634	Intermediate Similarity	NPD3667	Approved
0.7619	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD4767	Approved
0.7619	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD7128	Approved
0.7619	Intermediate Similarity	NPD5739	Approved
0.7619	Intermediate Similarity	NPD4768	Approved
0.7609	Intermediate Similarity	NPD4695	Discontinued
0.7593	Intermediate Similarity	NPD6617	Approved
0.7593	Intermediate Similarity	NPD5217	Approved
0.7593	Intermediate Similarity	NPD6847	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD5216	Approved
0.7593	Intermediate Similarity	NPD5215	Approved
0.7593	Intermediate Similarity	NPD8130	Phase 1
0.7593	Intermediate Similarity	NPD6869	Approved
0.7593	Intermediate Similarity	NPD5127	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7523	Intermediate Similarity	NPD6882	Approved
0.7523	Intermediate Similarity	NPD8297	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7477	Intermediate Similarity	NPD5168	Approved
0.7475	Intermediate Similarity	NPD7515	Phase 2
0.7474	Intermediate Similarity	NPD3665	Phase 1
0.7474	Intermediate Similarity	NPD4786	Approved
0.7474	Intermediate Similarity	NPD3133	Approved
0.7474	Intermediate Similarity	NPD3666	Approved
0.7455	Intermediate Similarity	NPD4632	Approved
0.7449	Intermediate Similarity	NPD4753	Phase 2
0.7426	Intermediate Similarity	NPD5210	Approved
0.7426	Intermediate Similarity	NPD4629	Approved
0.7423	Intermediate Similarity	NPD3573	Approved
0.7407	Intermediate Similarity	NPD6372	Approved
0.7407	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD5167	Approved
0.732	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5279	Phase 3
0.732	Intermediate Similarity	NPD5690	Phase 2
0.7292	Intermediate Similarity	NPD4197	Approved
0.7273	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6317	Approved
0.7257	Intermediate Similarity	NPD6009	Approved
0.7216	Intermediate Similarity	NPD5329	Approved
0.7204	Intermediate Similarity	NPD3617	Approved
0.7193	Intermediate Similarity	NPD6314	Approved
0.7193	Intermediate Similarity	NPD6313	Approved
0.7193	Intermediate Similarity	NPD6335	Approved
0.7157	Intermediate Similarity	NPD7748	Approved
0.713	Intermediate Similarity	NPD7100	Approved
0.713	Intermediate Similarity	NPD7101	Approved
0.7115	Intermediate Similarity	NPD7902	Approved
0.7083	Intermediate Similarity	NPD4223	Phase 3
0.7083	Intermediate Similarity	NPD4221	Approved
0.7069	Intermediate Similarity	NPD6319	Approved
0.7069	Intermediate Similarity	NPD6054	Approved
0.7041	Intermediate Similarity	NPD1696	Phase 3
0.7018	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD5983	Phase 2
0.7009	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6016	Approved
0.7009	Intermediate Similarity	NPD6015	Approved
0.697	Remote Similarity	NPD5280	Approved
0.697	Remote Similarity	NPD4519	Discontinued
0.697	Remote Similarity	NPD4623	Approved
0.697	Remote Similarity	NPD4694	Approved
0.6952	Remote Similarity	NPD6084	Phase 2
0.6952	Remote Similarity	NPD6083	Phase 2
0.6949	Remote Similarity	NPD6370	Approved
0.6949	Remote Similarity	NPD5988	Approved
0.6939	Remote Similarity	NPD3668	Phase 3
0.6931	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6399	Phase 3
0.6891	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3671	Phase 1
0.6833	Remote Similarity	NPD7492	Approved
0.6827	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7900	Approved
0.6818	Remote Similarity	NPD6008	Approved
0.68	Remote Similarity	NPD4688	Approved
0.68	Remote Similarity	NPD5205	Approved
0.68	Remote Similarity	NPD4689	Approved
0.68	Remote Similarity	NPD4690	Approved
0.68	Remote Similarity	NPD4693	Phase 3
0.68	Remote Similarity	NPD4138	Approved
0.678	Remote Similarity	NPD6059	Approved
0.6777	Remote Similarity	NPD6336	Discontinued
0.6777	Remote Similarity	NPD6616	Approved
0.6771	Remote Similarity	NPD4195	Approved
0.6762	Remote Similarity	NPD5695	Phase 3
0.6729	Remote Similarity	NPD5696	Approved
0.6723	Remote Similarity	NPD6909	Approved
0.6723	Remote Similarity	NPD6908	Approved
0.6721	Remote Similarity	NPD7078	Approved
0.6702	Remote Similarity	NPD3703	Phase 2
0.6701	Remote Similarity	NPD7525	Registered
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD6411	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6634	Remote Similarity	NPD5330	Approved
0.6634	Remote Similarity	NPD7146	Approved
0.6634	Remote Similarity	NPD6684	Approved
0.6634	Remote Similarity	NPD7334	Approved
0.6634	Remote Similarity	NPD6409	Approved
0.6634	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7645	Phase 2
0.6574	Remote Similarity	NPD5290	Discontinued
0.6571	Remote Similarity	NPD5133	Approved
0.6545	Remote Similarity	NPD5091	Approved
0.6545	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1694	Approved
0.6526	Remote Similarity	NPD7339	Approved
0.6526	Remote Similarity	NPD6942	Approved
0.6522	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6903	Approved
0.6475	Remote Similarity	NPD8328	Phase 3
0.6452	Remote Similarity	NPD4691	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6444	Remote Similarity	NPD7341	Phase 2
0.6442	Remote Similarity	NPD6904	Approved
0.6442	Remote Similarity	NPD6673	Approved
0.6442	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6080	Approved
0.6442	Remote Similarity	NPD6101	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.6421	Remote Similarity	NPD4058	Approved
0.6417	Remote Similarity	NPD4522	Approved
0.64	Remote Similarity	NPD6033	Approved
0.6389	Remote Similarity	NPD7614	Phase 1
0.6383	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7331	Phase 2
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6355	Remote Similarity	NPD5282	Discontinued
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4518	Approved
0.6344	Remote Similarity	NPD4137	Phase 3
0.6321	Remote Similarity	NPD5693	Phase 1
0.6321	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD6412	Phase 2
0.6311	Remote Similarity	NPD6098	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