NPASS Compound

Structure

NPC475313 OpenBabel07101718222D 38 41 0 0 1 0 0 0 0 0999 V2000 0.5000 -5.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -6.6430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2024 -4.0525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6398 -3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -4.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -4.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.0449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3125 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3614 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5933 -2.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3364 -1.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6887 -3.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7377 -3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0067 -0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5419 -2.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -4.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -4.0449 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.0556 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7498 -1.5292 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.1535 -1.7872 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0000 -3.1789 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.2024 -2.0962 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.8966 -2.4563 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.5908 -2.8164 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.9945 -3.0743 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8477 -2.1473 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.3829 -3.7946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.7769 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 2.5000 -5.7769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.7769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7749 -2.6325 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 13.1872 -2.5585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.1131 -1.1462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -5.7769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7009 -1.2202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -5.7769 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 12.4440 -1.8894 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 18 22 1 0 0 0 0 19 27 1 0 0 0 0 20 36 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 29 37 1 0 0 0 0 30 37 2 0 0 0 0 31 37 2 0 0 0 0 32 38 1 0 0 0 0 33 38 2 0 0 0 0 34 38 2 0 0 0 0 35 37 1 0 0 0 0 36 38 1 0 0 0 0 M CHG 2 29 -1 32 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.24
Volume:	552.179
LogP:	3.474
LogD:	1.532
LogS:	-5.082
# Rotatable Bonds:	10
TPSA:	153.09
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.323
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:	-4.792
MDCK Permeability:	2.4960978407762013e-05
Pgp-inhibitor:	0.803
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	97.22618865966797%
Volume Distribution (VD):	1.529
Pgp-substrate:	2.096050977706909%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.131
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	2.771
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.757
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.96
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.987
Carcinogencity:	0.921
Eye Corrosion:	0.957
Eye Irritation:	0.675
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC475313

Natural Product ID:	NPC475313
*Common Name:**	Cholest-5-Ene-1Beta,3Alpha,21-Triol 3,21-Disulfate
IUPAC Name:	disodium;[(1R,3S,8S,9S,10R,13S,14S,17R)-1-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-1-sulfonatooxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:
Standard InCHIKey:	RQFYJVCYYIOTMO-VIVOHZGTSA-L
Standard InCHI:	InChI=1S/C27H46O9S2.2Na/c1-17(2)6-5-7-18(16-35-37(29,30)31)22-10-11-23-21-9-8-19-14-20(36-38(32,33)34)15-25(28)27(19,4)24(21)12-13-26(22,23)3;;/h8,17-18,20-25,28H,5-7,9-16H2,1-4H3,(H,29,30,31)(H,32,33,34);;/q;2*+1/p-2/t18-,20-,21-,22+,23-,24-,25+,26+,27-;;/m0../s1
SMILES:	CC(C)CCCC(COS(=O)(=O)[O-])C1CCC2C1(CCC3C2CC=C4C3(C(CC(C4)OS(=O)(=O)[O-])O)C)C.[Na+].[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503339
PubChem CID:	44559768
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:0000260] Monohydroxy 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
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7853009]
NPO458	Ophiarachna incrassata	Species	Ophiodermatidae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	65000.0	nM	PMID[458322]

☑ 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 NPC475313 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	177
0.1-0.2	1591
0.2-0.3	6330
0.3-0.4	16302
0.4-0.5	7667
0.5-0.6	5897
0.6-0.7	3895
0.7-0.8	714
0.8-0.85	105
0.85-0.9	12
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC470383
0.9157	High Similarity	NPC478102
0.9091	High Similarity	NPC477605
0.8941	High Similarity	NPC477604
0.8889	High Similarity	NPC87604
0.8889	High Similarity	NPC475337
0.8721	High Similarity	NPC6391
0.8706	High Similarity	NPC124172
0.869	High Similarity	NPC1272
0.869	High Similarity	NPC101462
0.869	High Similarity	NPC470614
0.8675	High Similarity	NPC26117
0.8642	High Similarity	NPC240604
0.8642	High Similarity	NPC321381
0.8642	High Similarity	NPC107059
0.8642	High Similarity	NPC321016
0.8642	High Similarity	NPC300324
0.8636	High Similarity	NPC477606
0.8621	High Similarity	NPC477600
0.8588	High Similarity	NPC113978
0.8571	High Similarity	NPC209620
0.8571	High Similarity	NPC23852
0.8571	High Similarity	NPC473534
0.8537	High Similarity	NPC155986
0.8537	High Similarity	NPC318495
0.8537	High Similarity	NPC198968
0.8519	High Similarity	NPC136188
0.8519	High Similarity	NPC162742
0.8519	High Similarity	NPC288035
0.8519	High Similarity	NPC230301
0.8519	High Similarity	NPC304309
0.8519	High Similarity	NPC285893
0.8519	High Similarity	NPC22105
0.8519	High Similarity	NPC28657
0.8519	High Similarity	NPC134847
0.8506	High Similarity	NPC293287
0.8506	High Similarity	NPC478094
0.8506	High Similarity	NPC261266
0.8506	High Similarity	NPC24277
0.8506	High Similarity	NPC201273
0.8506	High Similarity	NPC152808
0.8488	Intermediate Similarity	NPC185568
0.8488	Intermediate Similarity	NPC209802
0.8488	Intermediate Similarity	NPC205845
0.8471	Intermediate Similarity	NPC30166
0.8471	Intermediate Similarity	NPC50964
0.8471	Intermediate Similarity	NPC248886
0.8444	Intermediate Similarity	NPC41554
0.8444	Intermediate Similarity	NPC97404
0.8434	Intermediate Similarity	NPC473943
0.8434	Intermediate Similarity	NPC275910
0.8434	Intermediate Similarity	NPC474216
0.8434	Intermediate Similarity	NPC477522
0.8427	Intermediate Similarity	NPC470361
0.8415	Intermediate Similarity	NPC113733
0.8415	Intermediate Similarity	NPC189883
0.8391	Intermediate Similarity	NPC470360
0.8391	Intermediate Similarity	NPC266511
0.8372	Intermediate Similarity	NPC110778
0.8353	Intermediate Similarity	NPC474531
0.8333	Intermediate Similarity	NPC80561
0.8333	Intermediate Similarity	NPC11216
0.8333	Intermediate Similarity	NPC3345
0.8333	Intermediate Similarity	NPC328714
0.8333	Intermediate Similarity	NPC472463
0.8333	Intermediate Similarity	NPC291484
0.8333	Intermediate Similarity	NPC143182
0.8333	Intermediate Similarity	NPC28862
0.8333	Intermediate Similarity	NPC109546
0.8333	Intermediate Similarity	NPC47982
0.8333	Intermediate Similarity	NPC81306
0.8333	Intermediate Similarity	NPC204188
0.8333	Intermediate Similarity	NPC84694
0.8333	Intermediate Similarity	NPC1319
0.8333	Intermediate Similarity	NPC329596
0.8315	Intermediate Similarity	NPC470542
0.8313	Intermediate Similarity	NPC34019
0.8313	Intermediate Similarity	NPC471798
0.8313	Intermediate Similarity	NPC214570
0.8295	Intermediate Similarity	NPC269058
0.8295	Intermediate Similarity	NPC299068
0.8295	Intermediate Similarity	NPC71520
0.8295	Intermediate Similarity	NPC6605
0.8295	Intermediate Similarity	NPC94462
0.8293	Intermediate Similarity	NPC257347
0.8293	Intermediate Similarity	NPC141071
0.8293	Intermediate Similarity	NPC471723
0.8276	Intermediate Similarity	NPC475798
0.8276	Intermediate Similarity	NPC469878
0.8276	Intermediate Similarity	NPC127606
0.8256	Intermediate Similarity	NPC49964
0.8256	Intermediate Similarity	NPC477599
0.8235	Intermediate Similarity	NPC322313
0.8235	Intermediate Similarity	NPC236112
0.8235	Intermediate Similarity	NPC241290
0.8235	Intermediate Similarity	NPC209944
0.8235	Intermediate Similarity	NPC164840
0.8235	Intermediate Similarity	NPC234193
0.8235	Intermediate Similarity	NPC236237
0.8235	Intermediate Similarity	NPC102253
0.8222	Intermediate Similarity	NPC105495
0.8214	Intermediate Similarity	NPC6978
0.8214	Intermediate Similarity	NPC244385
0.8214	Intermediate Similarity	NPC18603
0.8214	Intermediate Similarity	NPC167037
0.8214	Intermediate Similarity	NPC285761
0.8214	Intermediate Similarity	NPC76931
0.8214	Intermediate Similarity	NPC138621
0.8214	Intermediate Similarity	NPC31828
0.8214	Intermediate Similarity	NPC307965
0.8202	Intermediate Similarity	NPC149224
0.8193	Intermediate Similarity	NPC46160
0.8193	Intermediate Similarity	NPC129165
0.8193	Intermediate Similarity	NPC73875
0.8193	Intermediate Similarity	NPC237460
0.8193	Intermediate Similarity	NPC134330
0.8193	Intermediate Similarity	NPC96319
0.8193	Intermediate Similarity	NPC202642
0.8191	Intermediate Similarity	NPC477226
0.8171	Intermediate Similarity	NPC471797
0.8161	Intermediate Similarity	NPC193870
0.8161	Intermediate Similarity	NPC474634
0.8161	Intermediate Similarity	NPC477818
0.8161	Intermediate Similarity	NPC141941
0.8161	Intermediate Similarity	NPC232023
0.814	Intermediate Similarity	NPC82986
0.814	Intermediate Similarity	NPC474731
0.814	Intermediate Similarity	NPC474759
0.814	Intermediate Similarity	NPC474683
0.814	Intermediate Similarity	NPC264245
0.814	Intermediate Similarity	NPC47761
0.814	Intermediate Similarity	NPC242350
0.814	Intermediate Similarity	NPC7505
0.814	Intermediate Similarity	NPC474752
0.814	Intermediate Similarity	NPC320525
0.8132	Intermediate Similarity	NPC473956
0.8132	Intermediate Similarity	NPC470390
0.8132	Intermediate Similarity	NPC192437
0.8132	Intermediate Similarity	NPC270511
0.8132	Intermediate Similarity	NPC14380
0.8132	Intermediate Similarity	NPC295668
0.8132	Intermediate Similarity	NPC245410
0.8132	Intermediate Similarity	NPC475751
0.8118	Intermediate Similarity	NPC472742
0.8118	Intermediate Similarity	NPC273410
0.8118	Intermediate Similarity	NPC209430
0.8118	Intermediate Similarity	NPC80297
0.8118	Intermediate Similarity	NPC475727
0.8118	Intermediate Similarity	NPC116119
0.8118	Intermediate Similarity	NPC30986
0.8118	Intermediate Similarity	NPC80530
0.8111	Intermediate Similarity	NPC474668
0.8111	Intermediate Similarity	NPC475664
0.8111	Intermediate Similarity	NPC2158
0.8095	Intermediate Similarity	NPC477924
0.809	Intermediate Similarity	NPC474970
0.8085	Intermediate Similarity	NPC288970
0.8072	Intermediate Similarity	NPC322353
0.8072	Intermediate Similarity	NPC118508
0.8072	Intermediate Similarity	NPC121744
0.8068	Intermediate Similarity	NPC474493
0.8065	Intermediate Similarity	NPC127718
0.8065	Intermediate Similarity	NPC65402
0.8049	Intermediate Similarity	NPC474140
0.8049	Intermediate Similarity	NPC471799
0.8046	Intermediate Similarity	NPC201852
0.8046	Intermediate Similarity	NPC189972
0.8046	Intermediate Similarity	NPC5985
0.8046	Intermediate Similarity	NPC470049
0.8046	Intermediate Similarity	NPC7988
0.8043	Intermediate Similarity	NPC210268
0.8023	Intermediate Similarity	NPC13554
0.8023	Intermediate Similarity	NPC71535
0.8023	Intermediate Similarity	NPC324772
0.8023	Intermediate Similarity	NPC475679
0.8023	Intermediate Similarity	NPC78545
0.8022	Intermediate Similarity	NPC101886
0.8022	Intermediate Similarity	NPC31985
0.8022	Intermediate Similarity	NPC1015
0.8022	Intermediate Similarity	NPC109744
0.8	Intermediate Similarity	NPC477514
0.8	Intermediate Similarity	NPC474657
0.8	Intermediate Similarity	NPC316604
0.8	Intermediate Similarity	NPC186145
0.8	Intermediate Similarity	NPC85346
0.8	Intermediate Similarity	NPC148977
0.8	Intermediate Similarity	NPC186191
0.8	Intermediate Similarity	NPC302041
0.8	Intermediate Similarity	NPC205455
0.8	Intermediate Similarity	NPC177818
0.8	Intermediate Similarity	NPC271967
0.8	Intermediate Similarity	NPC65897
0.8	Intermediate Similarity	NPC478104
0.7979	Intermediate Similarity	NPC8774
0.7978	Intermediate Similarity	NPC318390
0.7978	Intermediate Similarity	NPC474349
0.7978	Intermediate Similarity	NPC157257
0.7978	Intermediate Similarity	NPC474189
0.7978	Intermediate Similarity	NPC274448
0.7976	Intermediate Similarity	NPC244488

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 NPC475313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1761
0.2-0.3	4493
0.3-0.4	1986
0.4-0.5	363
0.5-0.6	174
0.6-0.7	165
0.7-0.8	52
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD6942	Approved
0.8519	High Similarity	NPD7339	Approved
0.8235	Intermediate Similarity	NPD7525	Registered
0.8193	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6929	Approved
0.8023	Intermediate Similarity	NPD6931	Approved
0.8023	Intermediate Similarity	NPD6930	Phase 2
0.7955	Intermediate Similarity	NPD6695	Phase 3
0.7882	Intermediate Similarity	NPD5776	Phase 2
0.7882	Intermediate Similarity	NPD6925	Approved
0.7882	Intermediate Similarity	NPD6932	Approved
0.7865	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7145	Approved
0.7738	Intermediate Similarity	NPD6924	Approved
0.7738	Intermediate Similarity	NPD6926	Approved
0.7701	Intermediate Similarity	NPD7645	Phase 2
0.7701	Intermediate Similarity	NPD6683	Phase 2
0.7667	Intermediate Similarity	NPD3668	Phase 3
0.764	Intermediate Similarity	NPD3667	Approved
0.7614	Intermediate Similarity	NPD7514	Phase 3
0.7609	Intermediate Similarity	NPD7750	Discontinued
0.7609	Intermediate Similarity	NPD7524	Approved
0.7582	Intermediate Similarity	NPD6893	Approved
0.7558	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4785	Approved
0.7528	Intermediate Similarity	NPD6902	Approved
0.75	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD7152	Approved
0.75	Intermediate Similarity	NPD7150	Approved
0.75	Intermediate Similarity	NPD7151	Approved
0.747	Intermediate Similarity	NPD6923	Approved
0.747	Intermediate Similarity	NPD6922	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7416	Intermediate Similarity	NPD7332	Phase 2
0.7381	Intermediate Similarity	NPD7143	Approved
0.7381	Intermediate Similarity	NPD7144	Approved
0.7333	Intermediate Similarity	NPD6898	Phase 1
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7292	Intermediate Similarity	NPD6079	Approved
0.7292	Intermediate Similarity	NPD7087	Discontinued
0.7222	Intermediate Similarity	NPD4748	Discontinued
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7188	Intermediate Similarity	NPD7136	Phase 2
0.71	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD3665	Phase 1
0.7097	Intermediate Similarity	NPD3133	Approved
0.7097	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD4753	Phase 2
0.7045	Intermediate Similarity	NPD4190	Phase 3
0.7045	Intermediate Similarity	NPD5275	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7033	Intermediate Similarity	NPD7509	Discontinued
0.703	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5221	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6961	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD5286	Approved
0.6961	Remote Similarity	NPD4700	Approved
0.6961	Remote Similarity	NPD4696	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6939	Remote Similarity	NPD7637	Suspended
0.6931	Remote Similarity	NPD5173	Approved
0.6923	Remote Similarity	NPD4195	Approved
0.6863	Remote Similarity	NPD5290	Discontinued
0.686	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5225	Approved
0.6827	Remote Similarity	NPD5226	Approved
0.6827	Remote Similarity	NPD5224	Approved
0.6827	Remote Similarity	NPD5211	Phase 2
0.6827	Remote Similarity	NPD4633	Approved
0.6813	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4768	Approved
0.6792	Remote Similarity	NPD6675	Approved
0.6792	Remote Similarity	NPD5739	Approved
0.6792	Remote Similarity	NPD7128	Approved
0.6792	Remote Similarity	NPD6402	Approved
0.6792	Remote Similarity	NPD4767	Approved
0.6771	Remote Similarity	NPD5279	Phase 3
0.6768	Remote Similarity	NPD7515	Phase 2
0.6765	Remote Similarity	NPD6084	Phase 2
0.6765	Remote Similarity	NPD6083	Phase 2
0.6762	Remote Similarity	NPD5174	Approved
0.6762	Remote Similarity	NPD4754	Approved
0.6762	Remote Similarity	NPD5175	Approved
0.6759	Remote Similarity	NPD6372	Approved
0.6759	Remote Similarity	NPD6373	Approved
0.6733	Remote Similarity	NPD4629	Approved
0.6733	Remote Similarity	NPD5210	Approved
0.6731	Remote Similarity	NPD5223	Approved
0.6702	Remote Similarity	NPD4223	Phase 3
0.6702	Remote Similarity	NPD4221	Approved
0.6698	Remote Similarity	NPD5141	Approved
0.6697	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6579	Remote Similarity	NPD7328	Approved
0.6579	Remote Similarity	NPD7327	Approved
0.6577	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD6882	Approved
0.6574	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5697	Approved
0.6574	Remote Similarity	NPD5701	Approved
0.6566	Remote Similarity	NPD6051	Approved
0.6562	Remote Similarity	NPD4197	Approved
0.6545	Remote Similarity	NPD7102	Approved
0.6545	Remote Similarity	NPD6883	Approved
0.6545	Remote Similarity	NPD5249	Phase 3
0.6545	Remote Similarity	NPD7290	Approved
0.6545	Remote Similarity	NPD5248	Approved
0.6545	Remote Similarity	NPD5251	Approved
0.6545	Remote Similarity	NPD5247	Approved
0.6545	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD7516	Approved
0.6514	Remote Similarity	NPD5128	Approved
0.6486	Remote Similarity	NPD6617	Approved
0.6486	Remote Similarity	NPD8130	Phase 1
0.6486	Remote Similarity	NPD6847	Approved
0.6486	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6465	Remote Similarity	NPD6672	Approved
0.6465	Remote Similarity	NPD5737	Approved
0.6458	Remote Similarity	NPD4788	Approved
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6455	Remote Similarity	NPD6014	Approved
0.6452	Remote Similarity	NPD6114	Approved
0.6452	Remote Similarity	NPD6118	Approved
0.6452	Remote Similarity	NPD6115	Approved
0.6452	Remote Similarity	NPD6697	Approved
0.6436	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD4689	Approved
0.6429	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD4688	Approved
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD4693	Phase 3
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD5205	Approved
0.6429	Remote Similarity	NPD4690	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD4138	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD4159	Approved
0.641	Remote Similarity	NPD8296	Approved
0.641	Remote Similarity	NPD8380	Approved
0.641	Remote Similarity	NPD8033	Approved
0.641	Remote Similarity	NPD8379	Approved
0.641	Remote Similarity	NPD8335	Approved
0.641	Remote Similarity	NPD8378	Approved
0.6408	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD5696	Approved
0.6372	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD5168	Approved
0.6364	Remote Similarity	NPD6011	Approved
0.6355	Remote Similarity	NPD7632	Discontinued
0.6348	Remote Similarity	NPD7115	Discovery
0.6339	Remote Similarity	NPD5217	Approved
0.6339	Remote Similarity	NPD5215	Approved
0.6339	Remote Similarity	NPD5216	Approved
0.633	Remote Similarity	NPD6008	Approved
0.6325	Remote Similarity	NPD8377	Approved
0.6325	Remote Similarity	NPD6059	Approved
0.6325	Remote Similarity	NPD6054	Approved
0.6325	Remote Similarity	NPD6319	Approved
0.6325	Remote Similarity	NPD8294	Approved
0.6316	Remote Similarity	NPD4695	Discontinued
0.63	Remote Similarity	NPD4722	Approved
0.63	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD4723	Approved
0.6286	Remote Similarity	NPD7902	Approved
0.6277	Remote Similarity	NPD3617	Approved
0.6271	Remote Similarity	NPD7503	Approved
0.6263	Remote Similarity	NPD5280	Approved
0.6263	Remote Similarity	NPD4694	Approved
0.6263	Remote Similarity	NPD5690	Phase 2
0.625	Remote Similarity	NPD5169	Approved
0.6237	Remote Similarity	NPD6117	Approved
0.6226	Remote Similarity	NPD4225	Approved
0.6222	Remote Similarity	NPD4787	Phase 1
0.6218	Remote Similarity	NPD6370	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