NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	592.24
Volume:	560.97
LogP:	2.743
LogD:	1.076
LogS:	-3.654
# Rotatable Bonds:	10
TPSA:	173.32
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	5.53
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:	-4.949
MDCK Permeability:	1.32E-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	96.53%
Volume Distribution (VD):	1.471
Pgp-substrate:	2.02%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.338
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	1.836
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.869
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.818
Rat Oral Acute Toxicity:	0.768
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.984
Carcinogencity:	0.89
Eye Corrosion:	0.482
Eye Irritation:	0.253
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC477600

Natural Product ID:	NPC477600
*Common Name:**	5beta-Cholest-25-ene-3alpha,4alpha,5,21-tetraol 3,21-bis(sulfuric acid sodium) salt
IUPAC Name:	disodium;[(3R,4R,5R,8S,9S,10R,13S,14S,17R)-4,5-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyhept-6-en-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	KAIQQCDIMZMKJI-BOAXEGSRSA-L
Standard InCHI:	InChI=1S/C27H46O10S2.2Na/c1-17(2)6-5-7-18(16-36-38(30,31)32)20-8-9-21-19-10-15-27(29)24(28)23(37-39(33,34)35)12-14-26(27,4)22(19)11-13-25(20,21)3;;/h18-24,28-29H,1,5-16H2,2-4H3,(H,30,31,32)(H,33,34,35);;/q;2*+1/p-2/t18-,19-,20+,21-,22-,23+,24+,25+,26+,27-;;/m0../s1
SMILES:	CC(=C)CCC[C@@H](COS(=O)(=O)[O-])[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@]4([C@@]3(CC[C@H]([C@H]4O)OS(=O)(=O)[O-])C)O)C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	14238152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

*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
NPO33645	Ophilepis superba	Species	n.a.	n.a.	n.a.	Zampa, Okinawa, Japan	n.a.	PMID[8145229]
NPO33645	Ophilepis superba	Species	n.a.	n.a.	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	=	86000	nM	PMID[8145229]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	EC50	=	39000	nM	PMID[8145229]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	157000	nM	PMID[8145229]
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	IC50	>	157000	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 NPC477600 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	209
0.1-0.2	2524
0.2-0.3	8823
0.3-0.4	15568
0.4-0.5	6297
0.5-0.6	4996
0.6-0.7	3544
0.7-0.8	647
0.8-0.85	67
0.85-0.9	16
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9383	High Similarity	NPC477599
0.9268	High Similarity	NPC85095
0.9268	High Similarity	NPC216420
0.9268	High Similarity	NPC211135
0.8941	High Similarity	NPC121981
0.8889	High Similarity	NPC31828
0.8706	High Similarity	NPC255882
0.8667	High Similarity	NPC477605
0.8642	High Similarity	NPC91573
0.8642	High Similarity	NPC473916
0.8642	High Similarity	NPC477602
0.8642	High Similarity	NPC477601
0.8621	High Similarity	NPC475313
0.8588	High Similarity	NPC232023
0.8587	High Similarity	NPC477226
0.8554	High Similarity	NPC472742
0.8554	High Similarity	NPC80297
0.8554	High Similarity	NPC475727
0.8554	High Similarity	NPC116119
0.8523	High Similarity	NPC473436
0.8506	High Similarity	NPC269058
0.8506	High Similarity	NPC71520
0.8506	High Similarity	NPC477604
0.8452	Intermediate Similarity	NPC475679
0.8444	Intermediate Similarity	NPC219516
0.8434	Intermediate Similarity	NPC102708
0.8427	Intermediate Similarity	NPC109744
0.8395	Intermediate Similarity	NPC472503
0.8395	Intermediate Similarity	NPC308440
0.8387	Intermediate Similarity	NPC316604
0.8372	Intermediate Similarity	NPC478054
0.8372	Intermediate Similarity	NPC470929
0.8372	Intermediate Similarity	NPC207013
0.8333	Intermediate Similarity	NPC474132
0.8333	Intermediate Similarity	NPC475751
0.8333	Intermediate Similarity	NPC473956
0.8313	Intermediate Similarity	NPC202540
0.8295	Intermediate Similarity	NPC201273
0.8293	Intermediate Similarity	NPC158208
0.8293	Intermediate Similarity	NPC3403
0.8293	Intermediate Similarity	NPC243027
0.8293	Intermediate Similarity	NPC196136
0.8276	Intermediate Similarity	NPC469878
0.8276	Intermediate Similarity	NPC478102
0.8276	Intermediate Similarity	NPC86238
0.8256	Intermediate Similarity	NPC30166
0.8242	Intermediate Similarity	NPC275671
0.8235	Intermediate Similarity	NPC71535
0.8235	Intermediate Similarity	NPC78545
0.8235	Intermediate Similarity	NPC13554
0.8222	Intermediate Similarity	NPC477606
0.8214	Intermediate Similarity	NPC477819
0.8214	Intermediate Similarity	NPC301707
0.8214	Intermediate Similarity	NPC477817
0.8202	Intermediate Similarity	NPC186145
0.8202	Intermediate Similarity	NPC474657
0.8193	Intermediate Similarity	NPC93662
0.8193	Intermediate Similarity	NPC78067
0.8193	Intermediate Similarity	NPC278091
0.8171	Intermediate Similarity	NPC10476
0.8171	Intermediate Similarity	NPC228994
0.8171	Intermediate Similarity	NPC192501
0.8161	Intermediate Similarity	NPC113978
0.8148	Intermediate Similarity	NPC111234
0.8118	Intermediate Similarity	NPC476316
0.8111	Intermediate Similarity	NPC475664
0.8095	Intermediate Similarity	NPC192046
0.8095	Intermediate Similarity	NPC105208
0.8095	Intermediate Similarity	NPC477227
0.8095	Intermediate Similarity	NPC302578
0.8095	Intermediate Similarity	NPC128951
0.809	Intermediate Similarity	NPC94462
0.809	Intermediate Similarity	NPC478094
0.809	Intermediate Similarity	NPC6605
0.8072	Intermediate Similarity	NPC103822
0.8072	Intermediate Similarity	NPC240235
0.8072	Intermediate Similarity	NPC231256
0.8072	Intermediate Similarity	NPC104387
0.8072	Intermediate Similarity	NPC178383
0.8072	Intermediate Similarity	NPC185536
0.8072	Intermediate Similarity	NPC70982
0.8072	Intermediate Similarity	NPC230704
0.8072	Intermediate Similarity	NPC212879
0.8068	Intermediate Similarity	NPC320824
0.8068	Intermediate Similarity	NPC256567
0.8046	Intermediate Similarity	NPC7988
0.8043	Intermediate Similarity	NPC41554
0.8043	Intermediate Similarity	NPC97404
0.8025	Intermediate Similarity	NPC45296
0.8023	Intermediate Similarity	NPC102253
0.8023	Intermediate Similarity	NPC236112
0.8023	Intermediate Similarity	NPC322313
0.8023	Intermediate Similarity	NPC236237
0.8022	Intermediate Similarity	NPC105495
0.8022	Intermediate Similarity	NPC470361
0.8	Intermediate Similarity	NPC42853
0.8	Intermediate Similarity	NPC170978
0.8	Intermediate Similarity	NPC147993
0.8	Intermediate Similarity	NPC285761
0.8	Intermediate Similarity	NPC67657
0.8	Intermediate Similarity	NPC472500
0.8	Intermediate Similarity	NPC472342
0.8	Intermediate Similarity	NPC472499
0.8	Intermediate Similarity	NPC472501
0.8	Intermediate Similarity	NPC18857
0.7976	Intermediate Similarity	NPC86305
0.7976	Intermediate Similarity	NPC163597
0.7976	Intermediate Similarity	NPC14112
0.7959	Intermediate Similarity	NPC470601
0.7955	Intermediate Similarity	NPC110778
0.7952	Intermediate Similarity	NPC49168
0.7952	Intermediate Similarity	NPC62657
0.7952	Intermediate Similarity	NPC25511
0.7952	Intermediate Similarity	NPC192638
0.7952	Intermediate Similarity	NPC254509
0.7952	Intermediate Similarity	NPC145552
0.7952	Intermediate Similarity	NPC478130
0.7952	Intermediate Similarity	NPC5046
0.7952	Intermediate Similarity	NPC196358
0.7935	Intermediate Similarity	NPC11216
0.7935	Intermediate Similarity	NPC3345
0.7935	Intermediate Similarity	NPC291484
0.7935	Intermediate Similarity	NPC329596
0.7935	Intermediate Similarity	NPC204188
0.7935	Intermediate Similarity	NPC10274
0.7935	Intermediate Similarity	NPC80561
0.7935	Intermediate Similarity	NPC46758
0.7931	Intermediate Similarity	NPC470383
0.7931	Intermediate Similarity	NPC473534
0.7931	Intermediate Similarity	NPC474531
0.7927	Intermediate Similarity	NPC477821
0.7927	Intermediate Similarity	NPC323900
0.7927	Intermediate Similarity	NPC478103
0.7927	Intermediate Similarity	NPC473552
0.7927	Intermediate Similarity	NPC477823
0.7927	Intermediate Similarity	NPC324984
0.7927	Intermediate Similarity	NPC477822
0.7921	Intermediate Similarity	NPC474573
0.7912	Intermediate Similarity	NPC133588
0.7912	Intermediate Similarity	NPC474668
0.7907	Intermediate Similarity	NPC49599
0.7907	Intermediate Similarity	NPC273410
0.7907	Intermediate Similarity	NPC49627
0.7907	Intermediate Similarity	NPC80530
0.7907	Intermediate Similarity	NPC24504
0.7901	Intermediate Similarity	NPC107919
0.7895	Intermediate Similarity	NPC471903
0.7895	Intermediate Similarity	NPC111834
0.7895	Intermediate Similarity	NPC169270
0.7895	Intermediate Similarity	NPC292718
0.7895	Intermediate Similarity	NPC472989
0.7895	Intermediate Similarity	NPC306797
0.7889	Intermediate Similarity	NPC6391
0.7882	Intermediate Similarity	NPC331618
0.7882	Intermediate Similarity	NPC260301
0.7882	Intermediate Similarity	NPC212241
0.7882	Intermediate Similarity	NPC248830
0.7882	Intermediate Similarity	NPC119355
0.7882	Intermediate Similarity	NPC307336
0.7882	Intermediate Similarity	NPC257191
0.7882	Intermediate Similarity	NPC185915
0.7872	Intermediate Similarity	NPC277399
0.7865	Intermediate Similarity	NPC299963
0.7857	Intermediate Similarity	NPC200243
0.7857	Intermediate Similarity	NPC317242
0.7857	Intermediate Similarity	NPC470602
0.7849	Intermediate Similarity	NPC210268
0.7831	Intermediate Similarity	NPC153719
0.7831	Intermediate Similarity	NPC195489
0.7831	Intermediate Similarity	NPC95165
0.7826	Intermediate Similarity	NPC74258
0.7822	Intermediate Similarity	NPC475634
0.7816	Intermediate Similarity	NPC47149
0.7816	Intermediate Similarity	NPC22403
0.7812	Intermediate Similarity	NPC474994
0.7812	Intermediate Similarity	NPC274793
0.7812	Intermediate Similarity	NPC476040
0.7812	Intermediate Similarity	NPC476021
0.7802	Intermediate Similarity	NPC470620
0.7791	Intermediate Similarity	NPC138621
0.7791	Intermediate Similarity	NPC475
0.7791	Intermediate Similarity	NPC244385
0.7791	Intermediate Similarity	NPC167037
0.7791	Intermediate Similarity	NPC472502
0.7791	Intermediate Similarity	NPC6978
0.7789	Intermediate Similarity	NPC241047
0.7778	Intermediate Similarity	NPC244790
0.7778	Intermediate Similarity	NPC470360
0.7766	Intermediate Similarity	NPC291373
0.7765	Intermediate Similarity	NPC237460
0.7765	Intermediate Similarity	NPC63958
0.7755	Intermediate Similarity	NPC49532
0.7753	Intermediate Similarity	NPC193870
0.7753	Intermediate Similarity	NPC141941
0.7753	Intermediate Similarity	NPC477818
0.7738	Intermediate Similarity	NPC476736
0.7738	Intermediate Similarity	NPC304499
0.7732	Intermediate Similarity	NPC300179
0.7732	Intermediate Similarity	NPC102426
0.7727	Intermediate Similarity	NPC157655

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 NPC477600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	2811
0.2-0.3	4215
0.3-0.4	1341
0.4-0.5	274
0.5-0.6	170
0.6-0.7	155
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD7525	Registered
0.7901	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7524	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7241	Intermediate Similarity	NPD7339	Approved
0.7222	Intermediate Similarity	NPD6930	Phase 2
0.7222	Intermediate Similarity	NPD6931	Approved
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6695	Phase 3
0.7159	Intermediate Similarity	NPD6933	Approved
0.7111	Intermediate Similarity	NPD7645	Phase 2
0.7111	Intermediate Similarity	NPD6929	Approved
0.7097	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6932	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6926	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6923	Remote Similarity	NPD6683	Phase 2
0.6889	Remote Similarity	NPD6925	Approved
0.6889	Remote Similarity	NPD5776	Phase 2
0.6875	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7750	Discontinued
0.6848	Remote Similarity	NPD7514	Phase 3
0.6842	Remote Similarity	NPD6893	Approved
0.6814	Remote Similarity	NPD7516	Approved
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD7145	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.6809	Remote Similarity	NPD4788	Approved
0.6782	Remote Similarity	NPD4787	Phase 1
0.6768	Remote Similarity	NPD8035	Phase 2
0.6768	Remote Similarity	NPD8034	Phase 2
0.6737	Remote Similarity	NPD4786	Approved
0.6735	Remote Similarity	NPD5328	Approved
0.6726	Remote Similarity	NPD7327	Approved
0.6726	Remote Similarity	NPD7328	Approved
0.6705	Remote Similarity	NPD4243	Approved
0.6699	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4748	Discontinued
0.6635	Remote Similarity	NPD7640	Approved
0.6635	Remote Similarity	NPD7639	Approved
0.6602	Remote Similarity	NPD4755	Approved
0.66	Remote Similarity	NPD6079	Approved
0.66	Remote Similarity	NPD7087	Discontinued
0.6598	Remote Similarity	NPD3618	Phase 1
0.6596	Remote Similarity	NPD6902	Approved
0.6596	Remote Similarity	NPD6898	Phase 1
0.6593	Remote Similarity	NPD6117	Approved
0.6562	Remote Similarity	NPD3668	Phase 3
0.6556	Remote Similarity	NPD4785	Approved
0.6556	Remote Similarity	NPD4784	Approved
0.6552	Remote Similarity	NPD8335	Approved
0.6552	Remote Similarity	NPD8379	Approved
0.6552	Remote Similarity	NPD8378	Approved
0.6552	Remote Similarity	NPD8296	Approved
0.6552	Remote Similarity	NPD8380	Approved
0.6545	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD4202	Approved
0.6526	Remote Similarity	NPD3667	Approved
0.6522	Remote Similarity	NPD6116	Phase 1
0.6518	Remote Similarity	NPD8133	Approved
0.6517	Remote Similarity	NPD7150	Approved
0.6517	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7152	Approved
0.6517	Remote Similarity	NPD7151	Approved
0.65	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6700	Approved
0.6489	Remote Similarity	NPD7509	Discontinued
0.6484	Remote Similarity	NPD3703	Phase 2
0.6477	Remote Similarity	NPD6923	Approved
0.6477	Remote Similarity	NPD6922	Approved
0.6476	Remote Similarity	NPD5286	Approved
0.6476	Remote Similarity	NPD4700	Approved
0.6476	Remote Similarity	NPD4696	Approved
0.6476	Remote Similarity	NPD5285	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6452	Remote Similarity	NPD5364	Discontinued
0.6436	Remote Similarity	NPD6702	Approved
0.6436	Remote Similarity	NPD6703	Approved
0.6415	Remote Similarity	NPD4159	Approved
0.641	Remote Similarity	NPD8033	Approved
0.6404	Remote Similarity	NPD7143	Approved
0.6404	Remote Similarity	NPD7144	Approved
0.64	Remote Similarity	NPD4753	Phase 2
0.6374	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8171	Discontinued
0.6355	Remote Similarity	NPD5224	Approved
0.6355	Remote Similarity	NPD5211	Phase 2
0.6355	Remote Similarity	NPD5226	Approved
0.6355	Remote Similarity	NPD5225	Approved
0.6355	Remote Similarity	NPD4633	Approved
0.6346	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5222	Approved
0.6346	Remote Similarity	NPD5221	Approved
0.6346	Remote Similarity	NPD4697	Phase 3
0.6337	Remote Similarity	NPD7136	Phase 2
0.633	Remote Similarity	NPD4768	Approved
0.633	Remote Similarity	NPD6402	Approved
0.633	Remote Similarity	NPD4767	Approved
0.633	Remote Similarity	NPD7128	Approved
0.633	Remote Similarity	NPD6675	Approved
0.633	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6928	Phase 2
0.6306	Remote Similarity	NPD6372	Approved
0.6306	Remote Similarity	NPD6373	Approved
0.6304	Remote Similarity	NPD4190	Phase 3
0.6304	Remote Similarity	NPD5275	Approved
0.6296	Remote Similarity	NPD4754	Approved
0.6296	Remote Similarity	NPD5175	Approved
0.6296	Remote Similarity	NPD5174	Approved
0.6292	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5173	Approved
0.6283	Remote Similarity	NPD8297	Approved
0.6279	Remote Similarity	NPD371	Approved
0.6275	Remote Similarity	NPD7515	Phase 2
0.6262	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.6228	Remote Similarity	NPD4632	Approved
0.6226	Remote Similarity	NPD5290	Discontinued
0.6224	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD3133	Approved
0.6216	Remote Similarity	NPD7320	Approved
0.6216	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6899	Approved
0.6216	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD4729	Approved
0.6216	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD6399	Phase 3
0.6211	Remote Similarity	NPD4195	Approved
0.6204	Remote Similarity	NPD7632	Discontinued
0.6198	Remote Similarity	NPD7507	Approved
0.6195	Remote Similarity	NPD6649	Approved
0.6195	Remote Similarity	NPD6650	Approved
0.6186	Remote Similarity	NPD6319	Approved
0.618	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5360	Phase 3
0.6179	Remote Similarity	NPD7319	Approved
0.6161	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6882	Approved
0.6134	Remote Similarity	NPD7503	Approved
0.6132	Remote Similarity	NPD6084	Phase 2
0.6132	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD5697	Approved
0.6126	Remote Similarity	NPD5701	Approved
0.6126	Remote Similarity	NPD6412	Phase 2
0.6117	Remote Similarity	NPD7637	Suspended
0.6106	Remote Similarity	NPD5247	Approved
0.6106	Remote Similarity	NPD5248	Approved
0.6106	Remote Similarity	NPD5250	Approved
0.6106	Remote Similarity	NPD6883	Approved
0.6106	Remote Similarity	NPD7102	Approved
0.6106	Remote Similarity	NPD7290	Approved
0.6106	Remote Similarity	NPD5251	Approved
0.6106	Remote Similarity	NPD5249	Phase 3
0.6105	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5210	Approved
0.6095	Remote Similarity	NPD4629	Approved
0.6071	Remote Similarity	NPD5128	Approved
0.6068	Remote Similarity	NPD7115	Discovery
0.6053	Remote Similarity	NPD6617	Approved
0.6053	Remote Similarity	NPD6847	Approved
0.6053	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8130	Phase 1
0.6053	Remote Similarity	NPD6869	Approved
0.605	Remote Similarity	NPD6059	Approved
0.605	Remote Similarity	NPD6054	Approved
0.6044	Remote Similarity	NPD4245	Approved
0.6044	Remote Similarity	NPD4789	Approved
0.6044	Remote Similarity	NPD4244	Approved
0.602	Remote Similarity	NPD4223	Phase 3
0.602	Remote Similarity	NPD4221	Approved
0.6018	Remote Similarity	NPD6012	Approved
0.6018	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6014	Approved
0.6018	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5965	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5135	Approved
0.5965	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6370	Approved
0.5941	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD3698	Phase 2
0.5932	Remote Similarity	NPD6009	Approved
0.5929	Remote Similarity	NPD6011	Approved
0.5926	Remote Similarity	NPD4225	Approved
0.5922	Remote Similarity	NPD6051	Approved
0.5913	Remote Similarity	NPD5216	Approved
0.5913	Remote Similarity	NPD5215	Approved
0.5913	Remote Similarity	NPD5217	Approved
0.59	Remote Similarity	NPD4197	Approved
0.5868	Remote Similarity	NPD6016	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