NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	576.24
Volume:	552.179
LogP:	3.694
LogD:	1.436
LogS:	-6.06
# Rotatable Bonds:	9
TPSA:	153.09
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.24
Synthetic Accessibility Score:	5.487
Fsp3:	0.926
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:	-4.812
MDCK Permeability:	1.6215271898545325e-05
Pgp-inhibitor:	0.359
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	97.34664154052734%
Volume Distribution (VD):	1.944
Pgp-substrate:	2.498569965362549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.295
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	1.718
Half-life (T1/2):	0.003

ADMET: Toxicity

hERG Blockers:	0.442
Human Hepatotoxicity (H-HT):	0.552
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.958
Carcinogencity:	0.922
Eye Corrosion:	0.013
Eye Irritation:	0.02
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC478102

Natural Product ID:	NPC478102
*Common Name:**	disodium;[(3S,6S,10S,13S,17R)-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
IUPAC Name:	disodium;[(3S,6S,10S,13S,17R)-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-3-sulfonatooxy-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] sulfate
Synonyms:
Standard InCHIKey:	RQEBIZCBKDQKMI-CAINLFOGSA-L
Standard InCHI:	InChI=1S/C27H46O9S2.2Na/c1-16(2)6-9-24(28)17(3)20-7-8-21-19-15-25(36-38(32,33)34)23-14-18(35-37(29,30)31)10-12-27(23,5)22(19)11-13-26(20,21)4;;/h11,16-21,23-25,28H,6-10,12-15H2,1-5H3,(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/t17-,18-,19?,20+,21?,23?,24+,25-,26+,27+;;/m0../s1
SMILES:	C[C@@H]([C@H]1CCC2[C@@]1(CC=C3C2C[C@@H](C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)[O-])C)OS(=O)(=O)[O-])C)[C@@H](CCC(C)C)O.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL163896
PubChem CID:	24943515
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids

*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
NPO33662	Tremaster novaecaledonia	Species	Asterinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	=	19000	nM	PMID[8145229]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	=	128000	nM	PMID[8145229]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	161000	nM	PMID[8145229]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	IC50	>	161000	nM	PMID[8145229]

☑ 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 NPC478102 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	167
0.1-0.2	1588
0.2-0.3	7643
0.3-0.4	16155
0.4-0.5	6771
0.5-0.6	5612
0.6-0.7	3742
0.7-0.8	855
0.8-0.85	124
0.85-0.9	36
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9268	High Similarity	NPC477604
0.9157	High Similarity	NPC475313
0.9	High Similarity	NPC322313
0.9	High Similarity	NPC102253
0.9	High Similarity	NPC236237
0.8987	High Similarity	NPC244385
0.8987	High Similarity	NPC138621
0.8987	High Similarity	NPC6978
0.8987	High Similarity	NPC167037
0.8987	High Similarity	NPC475337
0.8974	High Similarity	NPC189883
0.8941	High Similarity	NPC477606
0.8889	High Similarity	NPC473534
0.8875	High Similarity	NPC80530
0.8875	High Similarity	NPC273410
0.8875	High Similarity	NPC1319
0.8861	High Similarity	NPC214570
0.8846	High Similarity	NPC257347
0.8846	High Similarity	NPC141071
0.8846	High Similarity	NPC471723
0.881	High Similarity	NPC478094
0.8795	High Similarity	NPC124172
0.878	High Similarity	NPC477599
0.878	High Similarity	NPC30166
0.8765	High Similarity	NPC236112
0.875	High Similarity	NPC285761
0.875	High Similarity	NPC275910
0.8734	High Similarity	NPC300324
0.8734	High Similarity	NPC46160
0.8734	High Similarity	NPC73875
0.8734	High Similarity	NPC321016
0.8734	High Similarity	NPC240604
0.8734	High Similarity	NPC321381
0.8734	High Similarity	NPC237460
0.8734	High Similarity	NPC107059
0.8734	High Similarity	NPC134330
0.8734	High Similarity	NPC129165
0.8734	High Similarity	NPC202642
0.8706	High Similarity	NPC478104
0.8675	High Similarity	NPC207013
0.8675	High Similarity	NPC110778
0.8659	High Similarity	NPC474531
0.8642	High Similarity	NPC30986
0.8642	High Similarity	NPC209430
0.8636	High Similarity	NPC475255
0.8625	High Similarity	NPC318495
0.8625	High Similarity	NPC155986
0.8625	High Similarity	NPC198968
0.8608	High Similarity	NPC230301
0.8608	High Similarity	NPC304309
0.8608	High Similarity	NPC322353
0.8608	High Similarity	NPC285893
0.8608	High Similarity	NPC121744
0.8608	High Similarity	NPC288035
0.8608	High Similarity	NPC28657
0.8608	High Similarity	NPC134847
0.8608	High Similarity	NPC22105
0.8608	High Similarity	NPC136188
0.8608	High Similarity	NPC162742
0.8608	High Similarity	NPC118508
0.859	High Similarity	NPC474140
0.8588	High Similarity	NPC24277
0.8571	High Similarity	NPC469878
0.8554	High Similarity	NPC470614
0.8554	High Similarity	NPC1272
0.8554	High Similarity	NPC101462
0.8554	High Similarity	NPC470049
0.8539	High Similarity	NPC477605
0.8537	High Similarity	NPC13554
0.8519	High Similarity	NPC302041
0.8519	High Similarity	NPC477522
0.8519	High Similarity	NPC85346
0.8519	High Similarity	NPC205455
0.8519	High Similarity	NPC186191
0.8519	High Similarity	NPC473943
0.8519	High Similarity	NPC474216
0.8519	High Similarity	NPC65897
0.8519	High Similarity	NPC87604
0.85	High Similarity	NPC113733
0.85	High Similarity	NPC470362
0.8471	Intermediate Similarity	NPC318390
0.8452	Intermediate Similarity	NPC193870
0.8452	Intermediate Similarity	NPC477818
0.8452	Intermediate Similarity	NPC141941
0.8434	Intermediate Similarity	NPC470383
0.8415	Intermediate Similarity	NPC143182
0.8415	Intermediate Similarity	NPC47982
0.8415	Intermediate Similarity	NPC81306
0.8415	Intermediate Similarity	NPC28862
0.8415	Intermediate Similarity	NPC328714
0.8415	Intermediate Similarity	NPC109546
0.8415	Intermediate Similarity	NPC84694
0.8395	Intermediate Similarity	NPC34019
0.8391	Intermediate Similarity	NPC470542
0.8375	Intermediate Similarity	NPC291503
0.8375	Intermediate Similarity	NPC3403
0.8372	Intermediate Similarity	NPC261266
0.8372	Intermediate Similarity	NPC201273
0.8372	Intermediate Similarity	NPC6391
0.8372	Intermediate Similarity	NPC474970
0.8354	Intermediate Similarity	NPC201373
0.8354	Intermediate Similarity	NPC182717
0.8353	Intermediate Similarity	NPC470077
0.8353	Intermediate Similarity	NPC475798
0.8353	Intermediate Similarity	NPC209802
0.8353	Intermediate Similarity	NPC185568
0.8353	Intermediate Similarity	NPC127606
0.8353	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC296701
0.8333	Intermediate Similarity	NPC49964
0.8333	Intermediate Similarity	NPC248886
0.8333	Intermediate Similarity	NPC20853
0.8333	Intermediate Similarity	NPC87489
0.8333	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC201852
0.8333	Intermediate Similarity	NPC218616
0.8313	Intermediate Similarity	NPC241290
0.8313	Intermediate Similarity	NPC234193
0.8313	Intermediate Similarity	NPC164840
0.8313	Intermediate Similarity	NPC209944
0.8313	Intermediate Similarity	NPC26117
0.8295	Intermediate Similarity	NPC105495
0.8293	Intermediate Similarity	NPC301707
0.8293	Intermediate Similarity	NPC76931
0.8293	Intermediate Similarity	NPC312328
0.8293	Intermediate Similarity	NPC318136
0.8293	Intermediate Similarity	NPC300499
0.8293	Intermediate Similarity	NPC477514
0.8293	Intermediate Similarity	NPC307965
0.8293	Intermediate Similarity	NPC18603
0.8276	Intermediate Similarity	NPC470620
0.8276	Intermediate Similarity	NPC477600
0.8272	Intermediate Similarity	NPC86305
0.8272	Intermediate Similarity	NPC247325
0.8272	Intermediate Similarity	NPC106432
0.8272	Intermediate Similarity	NPC244488
0.8272	Intermediate Similarity	NPC14112
0.8272	Intermediate Similarity	NPC96319
0.8272	Intermediate Similarity	NPC477925
0.8272	Intermediate Similarity	NPC274079
0.8256	Intermediate Similarity	NPC266511
0.825	Intermediate Similarity	NPC469593
0.825	Intermediate Similarity	NPC477138
0.825	Intermediate Similarity	NPC91858
0.825	Intermediate Similarity	NPC469534
0.825	Intermediate Similarity	NPC100334
0.825	Intermediate Similarity	NPC243342
0.825	Intermediate Similarity	NPC469533
0.8235	Intermediate Similarity	NPC113978
0.8235	Intermediate Similarity	NPC317458
0.8235	Intermediate Similarity	NPC474634
0.8228	Intermediate Similarity	NPC111234
0.8228	Intermediate Similarity	NPC167706
0.8228	Intermediate Similarity	NPC478103
0.8214	Intermediate Similarity	NPC6707
0.8214	Intermediate Similarity	NPC474752
0.8214	Intermediate Similarity	NPC7505
0.8214	Intermediate Similarity	NPC209620
0.8214	Intermediate Similarity	NPC474731
0.8214	Intermediate Similarity	NPC47761
0.8214	Intermediate Similarity	NPC474683
0.8214	Intermediate Similarity	NPC264245
0.8214	Intermediate Similarity	NPC474759
0.8214	Intermediate Similarity	NPC23852
0.8214	Intermediate Similarity	NPC82986
0.8193	Intermediate Similarity	NPC474132
0.8193	Intermediate Similarity	NPC472463
0.8182	Intermediate Similarity	NPC67872
0.8182	Intermediate Similarity	NPC133588
0.8182	Intermediate Similarity	NPC474668
0.8171	Intermediate Similarity	NPC90979
0.8171	Intermediate Similarity	NPC40394
0.8171	Intermediate Similarity	NPC130136
0.8171	Intermediate Similarity	NPC34177
0.8171	Intermediate Similarity	NPC471798
0.8171	Intermediate Similarity	NPC472805
0.8171	Intermediate Similarity	NPC101475
0.8171	Intermediate Similarity	NPC157996
0.8171	Intermediate Similarity	NPC477924
0.8161	Intermediate Similarity	NPC125399
0.8161	Intermediate Similarity	NPC299068
0.8161	Intermediate Similarity	NPC139724
0.8161	Intermediate Similarity	NPC6605
0.8161	Intermediate Similarity	NPC94462
0.8148	Intermediate Similarity	NPC231256
0.8148	Intermediate Similarity	NPC178383
0.8148	Intermediate Similarity	NPC212879
0.8148	Intermediate Similarity	NPC66566
0.8148	Intermediate Similarity	NPC185536
0.8148	Intermediate Similarity	NPC70982
0.8148	Intermediate Similarity	NPC230704
0.8148	Intermediate Similarity	NPC104387
0.8148	Intermediate Similarity	NPC477923
0.8148	Intermediate Similarity	NPC240235
0.814	Intermediate Similarity	NPC231310
0.814	Intermediate Similarity	NPC474047
0.8125	Intermediate Similarity	NPC471799
0.8118	Intermediate Similarity	NPC5985
0.8118	Intermediate Similarity	NPC50964
0.8118	Intermediate Similarity	NPC189972

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 NPC478102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1767
0.2-0.3	4575
0.3-0.4	1949
0.4-0.5	323
0.5-0.6	148
0.6-0.7	169
0.7-0.8	73
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7525	Registered
0.8608	High Similarity	NPD6942	Approved
0.8608	High Similarity	NPD7339	Approved
0.8272	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7645	Phase 2
0.7931	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD5328	Approved
0.7805	Intermediate Similarity	NPD6924	Approved
0.7805	Intermediate Similarity	NPD6926	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.7753	Intermediate Similarity	NPD3618	Phase 1
0.7727	Intermediate Similarity	NPD3668	Phase 3
0.7717	Intermediate Similarity	NPD6079	Approved
0.7701	Intermediate Similarity	NPD3667	Approved
0.7634	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD6933	Approved
0.759	Intermediate Similarity	NPD4784	Approved
0.759	Intermediate Similarity	NPD4785	Approved
0.7561	Intermediate Similarity	NPD7150	Approved
0.7561	Intermediate Similarity	NPD7152	Approved
0.7561	Intermediate Similarity	NPD7151	Approved
0.7531	Intermediate Similarity	NPD6923	Approved
0.7531	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7473	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7509	Discontinued
0.7471	Intermediate Similarity	NPD4748	Discontinued
0.7447	Intermediate Similarity	NPD6399	Phase 3
0.7439	Intermediate Similarity	NPD7144	Approved
0.7439	Intermediate Similarity	NPD7143	Approved
0.7396	Intermediate Similarity	NPD5222	Approved
0.7396	Intermediate Similarity	NPD4697	Phase 3
0.7396	Intermediate Similarity	NPD5221	Approved
0.7396	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6929	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD5286	Approved
0.7333	Intermediate Similarity	NPD3666	Approved
0.7333	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3665	Phase 1
0.7333	Intermediate Similarity	NPD3133	Approved
0.732	Intermediate Similarity	NPD5173	Approved
0.73	Intermediate Similarity	NPD4754	Approved
0.7294	Intermediate Similarity	NPD4190	Phase 3
0.7294	Intermediate Similarity	NPD5275	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7273	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5290	Discontinued
0.7222	Intermediate Similarity	NPD6695	Phase 3
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD4633	Approved
0.72	Intermediate Similarity	NPD5224	Approved
0.72	Intermediate Similarity	NPD5211	Phase 2
0.7159	Intermediate Similarity	NPD4195	Approved
0.7158	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD6402	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD4767	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD4768	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7128	Intermediate Similarity	NPD4753	Phase 2
0.7126	Intermediate Similarity	NPD6932	Approved
0.7126	Intermediate Similarity	NPD6925	Approved
0.7126	Intermediate Similarity	NPD5776	Phase 2
0.7115	Intermediate Similarity	NPD6372	Approved
0.7115	Intermediate Similarity	NPD6373	Approved
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7045	Intermediate Similarity	NPD7145	Approved
0.7019	Intermediate Similarity	NPD4729	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD4730	Approved
0.7	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD7639	Approved
0.6989	Remote Similarity	NPD5279	Phase 3
0.6981	Remote Similarity	NPD6649	Approved
0.6981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6650	Approved
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD8035	Phase 2
0.6966	Remote Similarity	NPD6683	Phase 2
0.6923	Remote Similarity	NPD4223	Phase 3
0.6923	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD4221	Approved
0.6916	Remote Similarity	NPD8297	Approved
0.6916	Remote Similarity	NPD6882	Approved
0.6915	Remote Similarity	NPD7750	Discontinued
0.6915	Remote Similarity	NPD7524	Approved
0.6897	Remote Similarity	NPD8264	Approved
0.6889	Remote Similarity	NPD7514	Phase 3
0.6887	Remote Similarity	NPD5135	Approved
0.6887	Remote Similarity	NPD5249	Phase 3
0.6887	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6887	Remote Similarity	NPD5251	Approved
0.6887	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5248	Approved
0.6887	Remote Similarity	NPD5250	Approved
0.6882	Remote Similarity	NPD6893	Approved
0.6882	Remote Similarity	NPD5329	Approved
0.6857	Remote Similarity	NPD5128	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6854	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7748	Approved
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6847	Approved
0.6813	Remote Similarity	NPD6902	Approved
0.6809	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7902	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6012	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6774	Remote Similarity	NPD4197	Approved
0.6771	Remote Similarity	NPD6051	Approved
0.6768	Remote Similarity	NPD5210	Approved
0.6768	Remote Similarity	NPD4629	Approved
0.6742	Remote Similarity	NPD6116	Phase 1
0.6729	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6703	Remote Similarity	NPD7332	Phase 2
0.6698	Remote Similarity	NPD5168	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6633	Remote Similarity	NPD7087	Discontinued
0.6632	Remote Similarity	NPD5205	Approved
0.6632	Remote Similarity	NPD4693	Phase 3
0.6632	Remote Similarity	NPD4688	Approved
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD4689	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD4690	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6632	Remote Similarity	NPD4138	Approved
0.663	Remote Similarity	NPD6898	Phase 1
0.6629	Remote Similarity	NPD6117	Approved
0.6628	Remote Similarity	NPD4787	Phase 1
0.6552	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4632	Approved
0.6531	Remote Similarity	NPD7136	Phase 2
0.6518	Remote Similarity	NPD6317	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7900	Approved
0.6495	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6903	Approved
0.6495	Remote Similarity	NPD4723	Approved
0.6495	Remote Similarity	NPD4722	Approved
0.6486	Remote Similarity	NPD5167	Approved
0.6484	Remote Similarity	NPD6114	Approved
0.6484	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6115	Approved
0.6484	Remote Similarity	NPD6118	Approved
0.6484	Remote Similarity	NPD3617	Approved
0.6465	Remote Similarity	NPD5281	Approved
0.6465	Remote Similarity	NPD5284	Approved
0.6463	Remote Similarity	NPD368	Approved
0.646	Remote Similarity	NPD6335	Approved
0.646	Remote Similarity	NPD7327	Approved
0.646	Remote Similarity	NPD7328	Approved
0.6458	Remote Similarity	NPD5690	Phase 2
0.6458	Remote Similarity	NPD4694	Approved
0.6458	Remote Similarity	NPD5280	Approved
0.6449	Remote Similarity	NPD6412	Phase 2
0.6436	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD6868	Approved
0.6408	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD7101	Approved
0.6404	Remote Similarity	NPD7100	Approved
0.6404	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7516	Approved
0.6381	Remote Similarity	NPD7632	Discontinued
0.6372	Remote Similarity	NPD6009	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