NPASS Compound

Structure

NPC473943 OpenBabel07101718182D 30 33 0 0 1 0 0 0 0 0999 V2000 1.5417 4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1816 5.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 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 0.8660 1.5000 0.0000 C 0 0 0 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8289 5.1974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4688 6.8916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1379 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 1 0 0 0 21 8 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 30 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	462.42
LogP:	5.908
LogD:	5.194
LogS:	-5.3
# Rotatable Bonds:	6
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	4.652
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.65
MDCK Permeability:	1.7750062397681177e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	97.14268493652344%
Volume Distribution (VD):	1.08
Pgp-substrate:	2.096407651901245%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.623
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.211
CYP2C9-substrate:	0.459
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	7.561
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.925
Carcinogencity:	0.525
Eye Corrosion:	0.116
Eye Irritation:	0.312
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473943

Natural Product ID:	NPC473943
*Common Name:**	24Xi-Hydroperoxycholesta-5,25-Dien-3Beta-Ol
IUPAC Name:	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	UEYFSWJEKNBMRD-GHMQSXNDSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-17(2)25(30-29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,18,20-25,28-29H,1,6,8-16H2,2-5H3/t18-,20+,21+,22-,23+,24+,25?,26+,27-/m1/s1
SMILES:	CC(CCC(C(=C)C)OO)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455877
PubChem CID:	10621860
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
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984148]
NPO33302	galaxaura marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322362]

☑ 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
ED50	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.33	ug ml-1	PMID[501385]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.64	ug ml-1	PMID[501385]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.43	ug ml-1	PMID[501385]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.26	ug ml-1	PMID[501385]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.26	ug ml-1	PMID[501386]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.33	ug ml-1	PMID[501386]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.64	ug ml-1	PMID[501386]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.43	ug ml-1	PMID[501386]

☑ 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 NPC473943 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	148
0.1-0.2	1277
0.2-0.3	6613
0.3-0.4	16008
0.4-0.5	7242
0.5-0.6	5822
0.6-0.7	4031
0.7-0.8	1168
0.8-0.85	235
0.85-0.9	72
0.9-0.95	54
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC474216
0.9722	High Similarity	NPC107059
0.9722	High Similarity	NPC321016
0.9722	High Similarity	NPC321381
0.96	High Similarity	NPC47761
0.9595	High Similarity	NPC81306
0.9595	High Similarity	NPC109546
0.9595	High Similarity	NPC84694
0.9595	High Similarity	NPC143182
0.9595	High Similarity	NPC28862
0.9595	High Similarity	NPC47982
0.9589	High Similarity	NPC155986
0.9589	High Similarity	NPC198968
0.9589	High Similarity	NPC318495
0.9583	High Similarity	NPC136188
0.9583	High Similarity	NPC285893
0.9583	High Similarity	NPC288035
0.9583	High Similarity	NPC134847
0.9583	High Similarity	NPC28657
0.9583	High Similarity	NPC304309
0.9583	High Similarity	NPC162742
0.9583	High Similarity	NPC22105
0.9583	High Similarity	NPC230301
0.9467	High Similarity	NPC234193
0.9467	High Similarity	NPC209944
0.9467	High Similarity	NPC164840
0.9467	High Similarity	NPC241290
0.9459	High Similarity	NPC87604
0.9459	High Similarity	NPC477522
0.9459	High Similarity	NPC477514
0.9452	High Similarity	NPC240604
0.9452	High Similarity	NPC300324
0.9452	High Similarity	NPC113733
0.9342	High Similarity	NPC474683
0.9342	High Similarity	NPC474752
0.9342	High Similarity	NPC209620
0.9342	High Similarity	NPC474759
0.9342	High Similarity	NPC264245
0.9342	High Similarity	NPC23852
0.9342	High Similarity	NPC7505
0.9342	High Similarity	NPC82986
0.9342	High Similarity	NPC474731
0.9333	High Similarity	NPC30986
0.9333	High Similarity	NPC209430
0.9333	High Similarity	NPC328714
0.9324	High Similarity	NPC34019
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC471723
0.9221	High Similarity	NPC101462
0.9221	High Similarity	NPC50964
0.9221	High Similarity	NPC189972
0.9221	High Similarity	NPC49964
0.9211	High Similarity	NPC26117
0.92	High Similarity	NPC76931
0.92	High Similarity	NPC307965
0.92	High Similarity	NPC18603
0.92	High Similarity	NPC275910
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC189883
0.9189	High Similarity	NPC247325
0.9189	High Similarity	NPC96319
0.9189	High Similarity	NPC244488
0.9189	High Similarity	NPC134330
0.9103	High Similarity	NPC475789
0.9103	High Similarity	NPC317458
0.9103	High Similarity	NPC474634
0.9091	High Similarity	NPC470383
0.9091	High Similarity	NPC474531
0.9079	High Similarity	NPC1319
0.9067	High Similarity	NPC214570
0.9041	High Similarity	NPC474140
0.9041	High Similarity	NPC471799
0.8987	High Similarity	NPC185568
0.8987	High Similarity	NPC205845
0.8974	High Similarity	NPC470614
0.8974	High Similarity	NPC5985
0.8974	High Similarity	NPC470049
0.8974	High Similarity	NPC1272
0.8961	High Similarity	NPC236112
0.8947	High Similarity	NPC167037
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC6978
0.8947	High Similarity	NPC138621
0.8947	High Similarity	NPC244385
0.8933	High Similarity	NPC237460
0.8933	High Similarity	NPC73875
0.8933	High Similarity	NPC202642
0.8933	High Similarity	NPC470362
0.8933	High Similarity	NPC46160
0.8919	High Similarity	NPC471797
0.8919	High Similarity	NPC469533
0.8919	High Similarity	NPC469534
0.8919	High Similarity	NPC469593
0.8875	High Similarity	NPC157257
0.8875	High Similarity	NPC266511
0.8875	High Similarity	NPC274448
0.8875	High Similarity	NPC318390
0.8831	High Similarity	NPC80530
0.8831	High Similarity	NPC273410
0.88	High Similarity	NPC322353
0.88	High Similarity	NPC121744
0.88	High Similarity	NPC118508
0.8765	High Similarity	NPC293287
0.8765	High Similarity	NPC152808
0.8765	High Similarity	NPC261266
0.8765	High Similarity	NPC6391
0.875	High Similarity	NPC209802
0.875	High Similarity	NPC59453
0.875	High Similarity	NPC33913
0.875	High Similarity	NPC238485
0.875	High Similarity	NPC472265
0.875	High Similarity	NPC124172
0.875	High Similarity	NPC474047
0.875	High Similarity	NPC160209
0.875	High Similarity	NPC221758
0.875	High Similarity	NPC208999
0.875	High Similarity	NPC470077
0.8734	High Similarity	NPC218616
0.8734	High Similarity	NPC201852
0.8734	High Similarity	NPC30166
0.8734	High Similarity	NPC296701
0.8734	High Similarity	NPC248886
0.8734	High Similarity	NPC87489
0.8734	High Similarity	NPC202389
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC167891
0.8701	High Similarity	NPC186191
0.8701	High Similarity	NPC85346
0.8701	High Similarity	NPC65897
0.8701	High Similarity	NPC205455
0.8701	High Similarity	NPC302041
0.8701	High Similarity	NPC83351
0.8667	High Similarity	NPC329090
0.8667	High Similarity	NPC243342
0.8667	High Similarity	NPC477138
0.8667	High Similarity	NPC27395
0.8659	High Similarity	NPC149224
0.8649	High Similarity	NPC242001
0.8642	High Similarity	NPC474349
0.8642	High Similarity	NPC474189
0.8625	High Similarity	NPC134481
0.8625	High Similarity	NPC470384
0.859	High Similarity	NPC472463
0.8571	High Similarity	NPC91594
0.8571	High Similarity	NPC471798
0.8554	High Similarity	NPC474668
0.8553	High Similarity	NPC291503
0.8553	High Similarity	NPC66566
0.8553	High Similarity	NPC471468
0.8553	High Similarity	NPC477923
0.8553	High Similarity	NPC319090
0.8553	High Similarity	NPC328104
0.8553	High Similarity	NPC185536
0.8537	High Similarity	NPC145879
0.8537	High Similarity	NPC51014
0.8537	High Similarity	NPC31564
0.8537	High Similarity	NPC94462
0.8537	High Similarity	NPC24277
0.8537	High Similarity	NPC474732
0.8537	High Similarity	NPC477604
0.8537	High Similarity	NPC474778
0.8537	High Similarity	NPC474733
0.8537	High Similarity	NPC155011
0.8537	High Similarity	NPC474970
0.8533	High Similarity	NPC182717
0.8533	High Similarity	NPC201373
0.8519	High Similarity	NPC478102
0.8519	High Similarity	NPC231310
0.8514	High Similarity	NPC475728
0.8514	High Similarity	NPC34834
0.8514	High Similarity	NPC145498
0.85	High Similarity	NPC20853
0.85	High Similarity	NPC151519
0.8462	Intermediate Similarity	NPC99168
0.8462	Intermediate Similarity	NPC470396
0.8462	Intermediate Similarity	NPC312328
0.8462	Intermediate Similarity	NPC475337
0.8462	Intermediate Similarity	NPC476314
0.8462	Intermediate Similarity	NPC474989
0.8462	Intermediate Similarity	NPC22955
0.8462	Intermediate Similarity	NPC318136
0.8452	Intermediate Similarity	NPC477606
0.8452	Intermediate Similarity	NPC470361
0.8452	Intermediate Similarity	NPC146554
0.8442	Intermediate Similarity	NPC315261
0.8442	Intermediate Similarity	NPC265588
0.8442	Intermediate Similarity	NPC477925
0.8442	Intermediate Similarity	NPC274079
0.8442	Intermediate Similarity	NPC106364
0.8434	Intermediate Similarity	NPC475313
0.8434	Intermediate Similarity	NPC58063
0.8434	Intermediate Similarity	NPC317590
0.8434	Intermediate Similarity	NPC475740
0.8421	Intermediate Similarity	NPC91858
0.8421	Intermediate Similarity	NPC100334
0.8415	Intermediate Similarity	NPC470360

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 NPC473943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1509
0.2-0.3	4410
0.3-0.4	2165
0.4-0.5	487
0.5-0.6	173
0.6-0.7	155
0.7-0.8	72
0.8-0.85	25
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9583	High Similarity	NPD7339	Approved
0.9583	High Similarity	NPD6942	Approved
0.9189	High Similarity	NPD3701	Clinical (unspecified phase)
0.875	High Similarity	NPD4786	Approved
0.8718	High Similarity	NPD7525	Registered
0.8667	High Similarity	NPD6926	Approved
0.8667	High Similarity	NPD6924	Approved
0.85	High Similarity	NPD3667	Approved
0.8442	Intermediate Similarity	NPD6933	Approved
0.8434	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4785	Approved
0.8421	Intermediate Similarity	NPD4784	Approved
0.84	Intermediate Similarity	NPD7150	Approved
0.84	Intermediate Similarity	NPD4243	Approved
0.84	Intermediate Similarity	NPD7152	Approved
0.84	Intermediate Similarity	NPD7151	Approved
0.8378	Intermediate Similarity	NPD6923	Approved
0.8378	Intermediate Similarity	NPD6922	Approved
0.8354	Intermediate Similarity	NPD6929	Approved
0.8267	Intermediate Similarity	NPD7144	Approved
0.8267	Intermediate Similarity	NPD7143	Approved
0.825	Intermediate Similarity	NPD6931	Approved
0.825	Intermediate Similarity	NPD6930	Phase 2
0.8125	Intermediate Similarity	NPD7645	Phase 2
0.8101	Intermediate Similarity	NPD5776	Phase 2
0.8101	Intermediate Similarity	NPD6925	Approved
0.8025	Intermediate Similarity	NPD4748	Discontinued
0.8023	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD7145	Approved
0.7952	Intermediate Similarity	NPD6695	Phase 3
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7875	Intermediate Similarity	NPD6932	Approved
0.7857	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3666	Approved
0.7857	Intermediate Similarity	NPD3133	Approved
0.7848	Intermediate Similarity	NPD4190	Phase 3
0.7848	Intermediate Similarity	NPD5275	Approved
0.7841	Intermediate Similarity	NPD6079	Approved
0.7805	Intermediate Similarity	NPD7514	Phase 3
0.7805	Intermediate Similarity	NPD7509	Discontinued
0.7778	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6893	Approved
0.7753	Intermediate Similarity	NPD6399	Phase 3
0.7711	Intermediate Similarity	NPD6902	Approved
0.7683	Intermediate Similarity	NPD4195	Approved
0.7683	Intermediate Similarity	NPD6683	Phase 2
0.7647	Intermediate Similarity	NPD3668	Phase 3
0.7625	Intermediate Similarity	NPD8264	Approved
0.759	Intermediate Similarity	NPD7332	Phase 2
0.7586	Intermediate Similarity	NPD7750	Discontinued
0.7586	Intermediate Similarity	NPD7524	Approved
0.7556	Intermediate Similarity	NPD4202	Approved
0.75	Intermediate Similarity	NPD6898	Phase 1
0.7471	Intermediate Similarity	NPD5279	Phase 3
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7412	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD4221	Approved
0.7356	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5329	Approved
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD4697	Phase 3
0.7312	Intermediate Similarity	NPD5222	Approved
0.7253	Intermediate Similarity	NPD7087	Discontinued
0.7241	Intermediate Similarity	NPD4197	Approved
0.7234	Intermediate Similarity	NPD5173	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD7638	Approved
0.7126	Intermediate Similarity	NPD4788	Approved
0.7113	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7079	Intermediate Similarity	NPD4688	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD4693	Phase 3
0.7079	Intermediate Similarity	NPD4689	Approved
0.7079	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD6084	Phase 2
0.7053	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5290	Discontinued
0.697	Remote Similarity	NPD5141	Approved
0.6941	Remote Similarity	NPD3617	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4723	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD4722	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6914	Remote Similarity	NPD4787	Phase 1
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6889	Remote Similarity	NPD4694	Approved
0.6889	Remote Similarity	NPD5280	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6882	Remote Similarity	NPD7637	Suspended
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6829	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4695	Discontinued
0.6774	Remote Similarity	NPD7136	Phase 2
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6707	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD4139	Approved
0.6705	Remote Similarity	NPD4692	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6098	Approved
0.6703	Remote Similarity	NPD4623	Approved
0.6703	Remote Similarity	NPD4519	Discontinued
0.6702	Remote Similarity	NPD8035	Phase 2
0.6702	Remote Similarity	NPD8034	Phase 2
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.6622	Remote Similarity	NPD342	Phase 1
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6585	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4137	Phase 3
0.6585	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD5284	Approved
0.6526	Remote Similarity	NPD5281	Approved
0.6512	Remote Similarity	NPD6117	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6506	Remote Similarity	NPD4244	Approved
0.6506	Remote Similarity	NPD4691	Approved
0.6506	Remote Similarity	NPD4789	Approved
0.6506	Remote Similarity	NPD4245	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6904	Approved
0.6489	Remote Similarity	NPD6080	Approved
0.6489	Remote Similarity	NPD6673	Approved
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5135	Approved
0.6471	Remote Similarity	NPD5733	Approved
0.6465	Remote Similarity	NPD4225	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