NPASS Compound

Structure

NPC33663 OpenBabel07101718332D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 1.0000 -0.0000 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 2.5981 2.5000 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 -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 0.8660 1.5000 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 0.0000 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 1 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 6 0 0 0 15 17 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 18 3 1 6 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 20 12 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.14
Volume:	357.761
LogP:	4.436
LogD:	4.005
LogS:	-4.844
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	5.252
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.459
MDCK Permeability:	4.1391114791622385e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.916
Plasma Protein Binding (PPB):	95.19157409667969%
Volume Distribution (VD):	1.439
Pgp-substrate:	5.393875598907471%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.312
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.246
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.911
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	9.723
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.379
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.571
Skin Sensitization:	0.915
Carcinogencity:	0.889
Eye Corrosion:	0.706
Eye Irritation:	0.162
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC33663

Natural Product ID:	NPC33663
*Common Name:**	Sphaerococcenol A
IUPAC Name:	(4S,4aS,4bS,8S,8aS,10aR)-8a-(bromomethyl)-4-hydroxy-4,10a-dimethyl-8-propan-2-yl-4a,4b,7,8,9,10-hexahydrophenanthren-3-one
Synonyms:
Standard InCHIKey:	MLAJPUJSVVNEHK-SYVORCANSA-N
Standard InCHI:	InChI=1S/C20H29BrO2/c1-13(2)14-6-5-7-15-17-18(3,10-11-20(14,15)12-21)9-8-16(22)19(17,4)23/h5,7-9,13-15,17,23H,6,10-12H2,1-4H3/t14-,15-,17-,18-,19+,20-/m0/s1
SMILES:	CC(C)[C@@H]1CC=C[C@H]2[C@H]3[C@@](C)(C=CC(=O)[C@@]3(C)O)CC[C@]12CBr
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459254
PubChem CID:	21775031
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
IC50	7

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3700.0	nM	PMID[474598]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	5200.0	nM	PMID[474598]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	3700.0	nM	PMID[474598]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	2800.0	nM	PMID[474598]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1000.0	nM	PMID[474597]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3200.0	nM	PMID[474598]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[474598]

☑ 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 NPC33663 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	181
0.1-0.2	1346
0.2-0.3	6984
0.3-0.4	15945
0.4-0.5	9223
0.5-0.6	6203
0.6-0.7	2428
0.7-0.8	363
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC108955
0.878	High Similarity	NPC55869
0.8588	High Similarity	NPC469993
0.8556	High Similarity	NPC474602
0.8554	High Similarity	NPC225515
0.8434	Intermediate Similarity	NPC476809
0.8409	Intermediate Similarity	NPC329643
0.8395	Intermediate Similarity	NPC92080
0.8395	Intermediate Similarity	NPC1254
0.8372	Intermediate Similarity	NPC132228
0.8372	Intermediate Similarity	NPC263997
0.8372	Intermediate Similarity	NPC8518
0.8313	Intermediate Similarity	NPC27817
0.8235	Intermediate Similarity	NPC103486
0.8214	Intermediate Similarity	NPC469637
0.8193	Intermediate Similarity	NPC275494
0.8193	Intermediate Similarity	NPC189485
0.8193	Intermediate Similarity	NPC30321
0.8193	Intermediate Similarity	NPC471409
0.8161	Intermediate Similarity	NPC241512
0.8161	Intermediate Similarity	NPC6185
0.814	Intermediate Similarity	NPC105803
0.814	Intermediate Similarity	NPC53733
0.8118	Intermediate Similarity	NPC474085
0.8068	Intermediate Similarity	NPC94666
0.8046	Intermediate Similarity	NPC144258
0.8	Intermediate Similarity	NPC2482
0.7976	Intermediate Similarity	NPC74410
0.7976	Intermediate Similarity	NPC476808
0.7955	Intermediate Similarity	NPC474537
0.7955	Intermediate Similarity	NPC474680
0.7952	Intermediate Similarity	NPC470525
0.7952	Intermediate Similarity	NPC110725
0.7907	Intermediate Similarity	NPC473217
0.7907	Intermediate Similarity	NPC116797
0.7907	Intermediate Similarity	NPC278459
0.7907	Intermediate Similarity	NPC121984
0.7889	Intermediate Similarity	NPC58271
0.7865	Intermediate Similarity	NPC472974
0.7857	Intermediate Similarity	NPC165711
0.7857	Intermediate Similarity	NPC266193
0.7857	Intermediate Similarity	NPC257666
0.7841	Intermediate Similarity	NPC237712
0.7826	Intermediate Similarity	NPC26865
0.7816	Intermediate Similarity	NPC302661
0.7816	Intermediate Similarity	NPC238991
0.7816	Intermediate Similarity	NPC193347
0.7802	Intermediate Similarity	NPC474918
0.7802	Intermediate Similarity	NPC65615
0.7802	Intermediate Similarity	NPC68148
0.7791	Intermediate Similarity	NPC26139
0.7778	Intermediate Similarity	NPC109900
0.7766	Intermediate Similarity	NPC147232
0.7765	Intermediate Similarity	NPC207772
0.7753	Intermediate Similarity	NPC133652
0.7753	Intermediate Similarity	NPC29447
0.775	Intermediate Similarity	NPC260474
0.775	Intermediate Similarity	NPC188292
0.7738	Intermediate Similarity	NPC186554
0.7738	Intermediate Similarity	NPC180886
0.7738	Intermediate Similarity	NPC76966
0.7738	Intermediate Similarity	NPC69143
0.7727	Intermediate Similarity	NPC49019
0.7717	Intermediate Similarity	NPC474209
0.7717	Intermediate Similarity	NPC475823
0.7717	Intermediate Similarity	NPC129913
0.7711	Intermediate Similarity	NPC22134
0.7701	Intermediate Similarity	NPC99308
0.7701	Intermediate Similarity	NPC471898
0.7692	Intermediate Similarity	NPC72397
0.7674	Intermediate Similarity	NPC170394
0.7674	Intermediate Similarity	NPC472490
0.7674	Intermediate Similarity	NPC192329
0.7667	Intermediate Similarity	NPC475022
0.7667	Intermediate Similarity	NPC222613
0.7667	Intermediate Similarity	NPC327115
0.7667	Intermediate Similarity	NPC118648
0.766	Intermediate Similarity	NPC23170
0.7647	Intermediate Similarity	NPC97377
0.764	Intermediate Similarity	NPC473246
0.764	Intermediate Similarity	NPC476412
0.7634	Intermediate Similarity	NPC99380
0.7634	Intermediate Similarity	NPC204341
0.7619	Intermediate Similarity	NPC192540
0.7619	Intermediate Similarity	NPC279666
0.7619	Intermediate Similarity	NPC175079
0.7614	Intermediate Similarity	NPC260956
0.7609	Intermediate Similarity	NPC310010
0.7609	Intermediate Similarity	NPC262043
0.7609	Intermediate Similarity	NPC326627
0.7609	Intermediate Similarity	NPC112454
0.7586	Intermediate Similarity	NPC18955
0.7586	Intermediate Similarity	NPC472478
0.7582	Intermediate Similarity	NPC230016
0.7582	Intermediate Similarity	NPC470523
0.7582	Intermediate Similarity	NPC136548
0.7582	Intermediate Similarity	NPC93778
0.7582	Intermediate Similarity	NPC58063
0.7558	Intermediate Similarity	NPC62336
0.7558	Intermediate Similarity	NPC179028
0.7556	Intermediate Similarity	NPC469948
0.7556	Intermediate Similarity	NPC476426
0.7556	Intermediate Similarity	NPC32037
0.7553	Intermediate Similarity	NPC134826
0.7553	Intermediate Similarity	NPC263780
0.7531	Intermediate Similarity	NPC87141
0.7529	Intermediate Similarity	NPC472305
0.7529	Intermediate Similarity	NPC263582
0.7529	Intermediate Similarity	NPC309399
0.7528	Intermediate Similarity	NPC102197
0.7528	Intermediate Similarity	NPC470015
0.7528	Intermediate Similarity	NPC477852
0.7528	Intermediate Similarity	NPC168188
0.75	Intermediate Similarity	NPC103958
0.75	Intermediate Similarity	NPC183503
0.75	Intermediate Similarity	NPC251970
0.75	Intermediate Similarity	NPC44963
0.75	Intermediate Similarity	NPC241854
0.75	Intermediate Similarity	NPC14151
0.75	Intermediate Similarity	NPC471791
0.75	Intermediate Similarity	NPC476046
0.75	Intermediate Similarity	NPC471793
0.75	Intermediate Similarity	NPC133921
0.75	Intermediate Similarity	NPC201912
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC471722
0.75	Intermediate Similarity	NPC226068
0.75	Intermediate Similarity	NPC161923
0.75	Intermediate Similarity	NPC283908
0.75	Intermediate Similarity	NPC48107
0.75	Intermediate Similarity	NPC470524
0.75	Intermediate Similarity	NPC38350
0.75	Intermediate Similarity	NPC472684
0.7474	Intermediate Similarity	NPC160413
0.7473	Intermediate Similarity	NPC472488
0.7473	Intermediate Similarity	NPC51014
0.7473	Intermediate Similarity	NPC472479
0.7473	Intermediate Similarity	NPC474733
0.7473	Intermediate Similarity	NPC31564
0.7473	Intermediate Similarity	NPC20688
0.7473	Intermediate Similarity	NPC474778
0.7473	Intermediate Similarity	NPC474732
0.7473	Intermediate Similarity	NPC194417
0.7473	Intermediate Similarity	NPC145879
0.7471	Intermediate Similarity	NPC215843
0.7471	Intermediate Similarity	NPC231431
0.7471	Intermediate Similarity	NPC474113
0.7471	Intermediate Similarity	NPC476177
0.747	Intermediate Similarity	NPC84790
0.7447	Intermediate Similarity	NPC174167
0.7447	Intermediate Similarity	NPC470036
0.7444	Intermediate Similarity	NPC329043
0.7444	Intermediate Similarity	NPC251170
0.7444	Intermediate Similarity	NPC161423
0.7444	Intermediate Similarity	NPC321187
0.7444	Intermediate Similarity	NPC227064
0.7444	Intermediate Similarity	NPC58841
0.7444	Intermediate Similarity	NPC214043
0.7444	Intermediate Similarity	NPC85774
0.7444	Intermediate Similarity	NPC96095
0.7442	Intermediate Similarity	NPC34110
0.7442	Intermediate Similarity	NPC197659
0.7442	Intermediate Similarity	NPC476608
0.7442	Intermediate Similarity	NPC472300
0.7419	Intermediate Similarity	NPC36668
0.7419	Intermediate Similarity	NPC477973
0.7419	Intermediate Similarity	NPC76879
0.7419	Intermediate Similarity	NPC474245
0.7419	Intermediate Similarity	NPC118011
0.7419	Intermediate Similarity	NPC119416
0.7416	Intermediate Similarity	NPC320514
0.7416	Intermediate Similarity	NPC48362
0.7416	Intermediate Similarity	NPC73882
0.7416	Intermediate Similarity	NPC251779
0.7416	Intermediate Similarity	NPC151519
0.7416	Intermediate Similarity	NPC310989
0.7416	Intermediate Similarity	NPC69101
0.7412	Intermediate Similarity	NPC476795
0.74	Intermediate Similarity	NPC111323
0.7396	Intermediate Similarity	NPC171395
0.7391	Intermediate Similarity	NPC475740
0.7391	Intermediate Similarity	NPC220930
0.7391	Intermediate Similarity	NPC136948
0.7391	Intermediate Similarity	NPC272039
0.7391	Intermediate Similarity	NPC476409
0.7391	Intermediate Similarity	NPC471792
0.7386	Intermediate Similarity	NPC37038
0.7386	Intermediate Similarity	NPC287063
0.7381	Intermediate Similarity	NPC247586
0.7375	Intermediate Similarity	NPC251118
0.7368	Intermediate Similarity	NPC250575
0.7368	Intermediate Similarity	NPC211230
0.7368	Intermediate Similarity	NPC474807
0.7368	Intermediate Similarity	NPC474736
0.7368	Intermediate Similarity	NPC233118
0.7363	Intermediate Similarity	NPC70685
0.7363	Intermediate Similarity	NPC311702
0.7363	Intermediate Similarity	NPC132629
0.7363	Intermediate Similarity	NPC15838
0.7363	Intermediate Similarity	NPC123319

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 NPC33663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1865
0.2-0.3	4163
0.3-0.4	2079
0.4-0.5	486
0.5-0.6	183
0.6-0.7	146
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8488	Intermediate Similarity	NPD5690	Phase 2
0.8434	Intermediate Similarity	NPD4695	Discontinued
0.8068	Intermediate Similarity	NPD5280	Approved
0.8068	Intermediate Similarity	NPD4694	Approved
0.8046	Intermediate Similarity	NPD4197	Approved
0.7955	Intermediate Similarity	NPD5329	Approved
0.7816	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4221	Approved
0.7765	Intermediate Similarity	NPD3617	Approved
0.7667	Intermediate Similarity	NPD4519	Discontinued
0.7667	Intermediate Similarity	NPD4623	Approved
0.7667	Intermediate Similarity	NPD5279	Phase 3
0.7609	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4753	Phase 2
0.7579	Intermediate Similarity	NPD5210	Approved
0.7579	Intermediate Similarity	NPD4629	Approved
0.7473	Intermediate Similarity	NPD4138	Approved
0.7473	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4693	Phase 3
0.7473	Intermediate Similarity	NPD4690	Approved
0.7473	Intermediate Similarity	NPD4689	Approved
0.7473	Intermediate Similarity	NPD5205	Approved
0.7473	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD4195	Approved
0.7447	Intermediate Similarity	NPD5281	Approved
0.7447	Intermediate Similarity	NPD5284	Approved
0.7444	Intermediate Similarity	NPD3665	Phase 1
0.7444	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3667	Approved
0.7396	Intermediate Similarity	NPD5695	Phase 3
0.7368	Intermediate Similarity	NPD5133	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4518	Approved
0.7283	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD4696	Approved
0.7273	Intermediate Similarity	NPD5285	Approved
0.7263	Intermediate Similarity	NPD6079	Approved
0.7263	Intermediate Similarity	NPD5694	Approved
0.7253	Intermediate Similarity	NPD4786	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD3573	Approved
0.72	Intermediate Similarity	NPD5223	Approved
0.7158	Intermediate Similarity	NPD4096	Approved
0.7158	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD4691	Approved
0.7129	Intermediate Similarity	NPD5224	Approved
0.7129	Intermediate Similarity	NPD5211	Phase 2
0.7129	Intermediate Similarity	NPD5226	Approved
0.7129	Intermediate Similarity	NPD5091	Approved
0.7129	Intermediate Similarity	NPD4633	Approved
0.7129	Intermediate Similarity	NPD5225	Approved
0.7111	Intermediate Similarity	NPD4692	Approved
0.7111	Intermediate Similarity	NPD4139	Approved
0.7093	Intermediate Similarity	NPD4687	Approved
0.7093	Intermediate Similarity	NPD4058	Approved
0.7083	Intermediate Similarity	NPD6050	Approved
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7059	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5175	Approved
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.7024	Intermediate Similarity	NPD4137	Phase 3
0.701	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD5141	Approved
0.6979	Remote Similarity	NPD5207	Approved
0.697	Remote Similarity	NPD4697	Phase 3
0.6947	Remote Similarity	NPD6672	Approved
0.6947	Remote Similarity	NPD5737	Approved
0.6941	Remote Similarity	NPD4747	Approved
0.6931	Remote Similarity	NPD4700	Approved
0.6915	Remote Similarity	NPD6098	Approved
0.6907	Remote Similarity	NPD5693	Phase 1
0.6907	Remote Similarity	NPD7515	Phase 2
0.6897	Remote Similarity	NPD5733	Approved
0.6882	Remote Similarity	NPD3668	Phase 3
0.6867	Remote Similarity	NPD7331	Phase 2
0.686	Remote Similarity	NPD5276	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6818	Remote Similarity	NPD6274	Approved
0.6813	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7614	Phase 1
0.6792	Remote Similarity	NPD4729	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD6881	Approved
0.6792	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4788	Approved
0.6771	Remote Similarity	NPD5208	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6747	Remote Similarity	NPD7341	Phase 2
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6731	Remote Similarity	NPD4754	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6707	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4784	Approved
0.6705	Remote Similarity	NPD4785	Approved
0.67	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6632	Remote Similarity	NPD1696	Phase 3
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD5217	Approved
0.6606	Remote Similarity	NPD5215	Approved
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD5216	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6649	Approved
0.6604	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD6675	Approved
0.6604	Remote Similarity	NPD7128	Approved
0.6604	Remote Similarity	NPD6402	Approved
0.6604	Remote Similarity	NPD4767	Approved
0.6598	Remote Similarity	NPD6903	Approved
0.6598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5959	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6545	Remote Similarity	NPD8297	Approved
0.6545	Remote Similarity	NPD6882	Approved
0.6542	Remote Similarity	NPD5701	Approved
0.6512	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD7320	Approved
0.6477	Remote Similarity	NPD4243	Approved
0.6442	Remote Similarity	NPD6404	Discontinued
0.6436	Remote Similarity	NPD5282	Discontinued
0.6436	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD5167	Approved
0.6422	Remote Similarity	NPD6372	Approved
0.6422	Remote Similarity	NPD6373	Approved
0.64	Remote Similarity	NPD6411	Approved
0.6389	Remote Similarity	NPD6614	Approved
0.6383	Remote Similarity	NPD8028	Phase 2
0.6374	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6009	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7732	Phase 3
0.6306	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD1694	Approved
0.6279	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7900	Approved
0.6264	Remote Similarity	NPD4190	Phase 3
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD5275	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6261	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.6261	Remote Similarity	NPD6335	Approved
0.6237	Remote Similarity	NPD3671	Phase 1
0.6228	Remote Similarity	NPD6868	Approved
0.622	Remote Similarity	NPD287	Approved
0.6207	Remote Similarity	NPD7101	Approved
0.6207	Remote Similarity	NPD4522	Approved
0.6207	Remote Similarity	NPD7100	Approved
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4789	Approved
0.6174	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD6054	Approved
0.6154	Remote Similarity	NPD6319	Approved
0.6136	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5360	Phase 3
0.6102	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6015	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