NPASS Compound

Structure

CID160583 OpenBabel06191715532D 28 32 0 0 1 0 0 0 0 0999 V2000 -0.8124 -2.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7161 -0.9908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6860 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5285 -3.4061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 0.9728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6858 -2.9199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 1.4592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0139 -1.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3718 -1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 -1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1784 0.2368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5277 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 -1.4602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3715 -2.9194 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6855 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8430 -0.4867 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0005 -1.9466 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9651 -1.1259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8430 -1.4602 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6861 -1.9469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8425 -0.4864 0.0000 C 0 0 1 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 -4.2376 -3.4194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -2.9466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6877 -1.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0667 -0.1588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 14 1 0 0 0 0 4 17 1 0 0 0 0 5 7 1 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 28 1 0 0 0 0 13 16 1 0 0 0 0 14 21 1 1 0 0 0 15 24 1 6 0 0 0 16 22 1 6 0 0 0 17 20 1 0 0 0 0 17 23 1 1 0 0 0 18 20 1 0 0 0 0 18 25 1 1 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 6 0 0 0 21 1 1 6 0 0 0 22 23 1 6 0 0 0 23 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.24
Volume:	402.26
LogP:	3.1
LogD:	2.739
LogS:	-3.821
# Rotatable Bonds:	1
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.903
Fsp3:	0.826
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.299
MDCK Permeability:	5.587839041254483e-06
Pgp-inhibitor:	0.007
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.338
Plasma Protein Binding (PPB):	94.32723236083984%
Volume Distribution (VD):	1.124
Pgp-substrate:	7.647580623626709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.561
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.575
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	11.416
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.353
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.775
Carcinogencity:	0.355
Eye Corrosion:	0.005
Eye Irritation:	0.028
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC160583

Natural Product ID:	NPC160583
*Common Name:**	Sarmentogenin
IUPAC Name:	3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:	Sarmentogenin
Standard InCHIKey:	FLMSQRUGSHIKCT-DDZQJACLSA-N
Standard InCHI:	InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-20(21)18(25)11-22(2)16(6-8-23(17,22)27)13-9-19(26)28-12-13/h9,14-18,20,24-25,27H,3-8,10-12H2,1-2H3/t14-,15+,16-,17-,18-,20-,21+,22-,23+/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2[C@H](O)C[C@]2([C@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1075814
PubChem CID:	6437
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides 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
NPO5716	Mallotus nudiflorus	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1002/hlca.200590219]
NPO5716	Mallotus nudiflorus	Species	Euphorbiaceae	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
Others	5

Activity Type	# Activity
Cell Line	2
Individual Protein	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Survival	=	26.0	%	PMID[507838]
NPT139	Cell Line	HT-29	Homo sapiens	Survival	=	63.0	%	PMID[507838]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Survival	=	4.0	%	PMID[507838]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	70.58	%	PMID[507839]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	105.75	%	PMID[507839]

☑ 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 NPC160583 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	196
0.1-0.2	1392
0.2-0.3	4669
0.3-0.4	10937
0.4-0.5	10668
0.5-0.6	5881
0.6-0.7	6025
0.7-0.8	2596
0.8-0.85	237
0.85-0.9	78
0.9-0.95	2
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC268829
0.9789	High Similarity	NPC25177
0.9789	High Similarity	NPC247701
0.9789	High Similarity	NPC295110
0.9789	High Similarity	NPC222875
0.9592	High Similarity	NPC119855
0.9592	High Similarity	NPC220217
0.9588	High Similarity	NPC196471
0.9588	High Similarity	NPC10232
0.9588	High Similarity	NPC97487
0.9588	High Similarity	NPC189588
0.9588	High Similarity	NPC187302
0.9588	High Similarity	NPC472821
0.9394	High Similarity	NPC186668
0.9158	High Similarity	NPC105490
0.9118	High Similarity	NPC475030
0.9072	High Similarity	NPC231751
0.9053	High Similarity	NPC7349
0.8889	High Similarity	NPC251680
0.8868	High Similarity	NPC471633
0.8868	High Similarity	NPC31354
0.8868	High Similarity	NPC84949
0.8868	High Similarity	NPC69576
0.8824	High Similarity	NPC472818
0.88	High Similarity	NPC11974
0.8796	High Similarity	NPC83287
0.8785	High Similarity	NPC99620
0.8785	High Similarity	NPC199428
0.8785	High Similarity	NPC5311
0.8785	High Similarity	NPC310341
0.8785	High Similarity	NPC193382
0.8763	High Similarity	NPC201725
0.8738	High Similarity	NPC472820
0.8725	High Similarity	NPC472819
0.8704	High Similarity	NPC50305
0.8704	High Similarity	NPC473852
0.8704	High Similarity	NPC474418
0.8704	High Similarity	NPC243196
0.8704	High Similarity	NPC77319
0.8704	High Similarity	NPC27507
0.8704	High Similarity	NPC34390
0.8704	High Similarity	NPC142066
0.8704	High Similarity	NPC196429
0.8704	High Similarity	NPC158344
0.8704	High Similarity	NPC290693
0.8704	High Similarity	NPC471353
0.8704	High Similarity	NPC157376
0.8704	High Similarity	NPC471351
0.8704	High Similarity	NPC87250
0.8704	High Similarity	NPC309034
0.8704	High Similarity	NPC93883
0.8704	High Similarity	NPC471354
0.8704	High Similarity	NPC244402
0.8704	High Similarity	NPC152615
0.8704	High Similarity	NPC84987
0.8704	High Similarity	NPC471355
0.8704	High Similarity	NPC99728
0.87	High Similarity	NPC472826
0.87	High Similarity	NPC324841
0.8687	High Similarity	NPC51499
0.8673	High Similarity	NPC276110
0.8667	High Similarity	NPC103491
0.8667	High Similarity	NPC12795
0.8641	High Similarity	NPC295843
0.8627	High Similarity	NPC112009
0.8611	High Similarity	NPC196931
0.8611	High Similarity	NPC72772
0.8611	High Similarity	NPC469794
0.86	High Similarity	NPC325229
0.86	High Similarity	NPC275086
0.86	High Similarity	NPC218107
0.8598	High Similarity	NPC171126
0.8586	High Similarity	NPC253115
0.8586	High Similarity	NPC304899
0.8558	High Similarity	NPC471205
0.8558	High Similarity	NPC475781
0.8557	High Similarity	NPC130840
0.8557	High Similarity	NPC234335
0.8545	High Similarity	NPC30483
0.8545	High Similarity	NPC470897
0.8545	High Similarity	NPC304260
0.8545	High Similarity	NPC5883
0.8545	High Similarity	NPC236973
0.8545	High Similarity	NPC329905
0.8545	High Similarity	NPC32177
0.8545	High Similarity	NPC469756
0.8545	High Similarity	NPC29639
0.8545	High Similarity	NPC292467
0.8545	High Similarity	NPC44899
0.8545	High Similarity	NPC55532
0.8544	High Similarity	NPC200861
0.8532	High Similarity	NPC203862
0.8529	High Similarity	NPC475038
0.8529	High Similarity	NPC109195
0.8515	High Similarity	NPC201406
0.8505	High Similarity	NPC44537
0.8491	Intermediate Similarity	NPC179642
0.8482	Intermediate Similarity	NPC264336
0.8476	Intermediate Similarity	NPC88701
0.8476	Intermediate Similarity	NPC137462
0.8476	Intermediate Similarity	NPC304276
0.8468	Intermediate Similarity	NPC257610
0.8468	Intermediate Similarity	NPC474466
0.8468	Intermediate Similarity	NPC475629
0.8468	Intermediate Similarity	NPC475556
0.8468	Intermediate Similarity	NPC475136
0.8468	Intermediate Similarity	NPC72260
0.8462	Intermediate Similarity	NPC51719
0.8454	Intermediate Similarity	NPC302280
0.8447	Intermediate Similarity	NPC180204
0.8447	Intermediate Similarity	NPC171014
0.8447	Intermediate Similarity	NPC473523
0.8447	Intermediate Similarity	NPC45897
0.8447	Intermediate Similarity	NPC281378
0.8431	Intermediate Similarity	NPC475617
0.8416	Intermediate Similarity	NPC278673
0.84	Intermediate Similarity	NPC194132
0.8396	Intermediate Similarity	NPC75389
0.8393	Intermediate Similarity	NPC173555
0.8393	Intermediate Similarity	NPC475590
0.8393	Intermediate Similarity	NPC120390
0.8393	Intermediate Similarity	NPC474908
0.8393	Intermediate Similarity	NPC475419
0.8393	Intermediate Similarity	NPC231518
0.8393	Intermediate Similarity	NPC314535
0.8393	Intermediate Similarity	NPC40749
0.8393	Intermediate Similarity	NPC475219
0.8384	Intermediate Similarity	NPC3359
0.8384	Intermediate Similarity	NPC140277
0.8381	Intermediate Similarity	NPC43063
0.8381	Intermediate Similarity	NPC79298
0.8367	Intermediate Similarity	NPC329842
0.8365	Intermediate Similarity	NPC473543
0.8365	Intermediate Similarity	NPC472822
0.8351	Intermediate Similarity	NPC473647
0.835	Intermediate Similarity	NPC22388
0.835	Intermediate Similarity	NPC475344
0.835	Intermediate Similarity	NPC476471
0.835	Intermediate Similarity	NPC162973
0.8333	Intermediate Similarity	NPC208358
0.8333	Intermediate Similarity	NPC470063
0.8333	Intermediate Similarity	NPC38855
0.8319	Intermediate Similarity	NPC193893
0.8319	Intermediate Similarity	NPC474423
0.8319	Intermediate Similarity	NPC74259
0.8319	Intermediate Similarity	NPC115349
0.8317	Intermediate Similarity	NPC210337
0.8317	Intermediate Similarity	NPC475032
0.8317	Intermediate Similarity	NPC475033
0.8316	Intermediate Similarity	NPC474013
0.8304	Intermediate Similarity	NPC145074
0.8304	Intermediate Similarity	NPC114939
0.8304	Intermediate Similarity	NPC41123
0.8302	Intermediate Similarity	NPC275060
0.83	Intermediate Similarity	NPC329435
0.8288	Intermediate Similarity	NPC218093
0.8288	Intermediate Similarity	NPC16701
0.8286	Intermediate Similarity	NPC471206
0.8269	Intermediate Similarity	NPC474124
0.8269	Intermediate Similarity	NPC36688
0.8269	Intermediate Similarity	NPC120009
0.8265	Intermediate Similarity	NPC219937
0.8265	Intermediate Similarity	NPC194485
0.8265	Intermediate Similarity	NPC53890
0.8265	Intermediate Similarity	NPC78973
0.8265	Intermediate Similarity	NPC123252
0.8252	Intermediate Similarity	NPC471412
0.8252	Intermediate Similarity	NPC155974
0.8247	Intermediate Similarity	NPC160304
0.8246	Intermediate Similarity	NPC208193
0.8246	Intermediate Similarity	NPC27363
0.8246	Intermediate Similarity	NPC308262
0.8246	Intermediate Similarity	NPC117445
0.8241	Intermediate Similarity	NPC470076
0.8241	Intermediate Similarity	NPC183603
0.8235	Intermediate Similarity	NPC181147
0.8229	Intermediate Similarity	NPC131813
0.8218	Intermediate Similarity	NPC475380
0.8218	Intermediate Similarity	NPC276103
0.8218	Intermediate Similarity	NPC209297
0.8218	Intermediate Similarity	NPC54248
0.8218	Intermediate Similarity	NPC88009
0.8214	Intermediate Similarity	NPC291820
0.8214	Intermediate Similarity	NPC213761
0.8214	Intermediate Similarity	NPC153085
0.8214	Intermediate Similarity	NPC268326
0.8214	Intermediate Similarity	NPC35171
0.8214	Intermediate Similarity	NPC81222
0.8214	Intermediate Similarity	NPC278681
0.8208	Intermediate Similarity	NPC122816
0.8208	Intermediate Similarity	NPC475074
0.82	Intermediate Similarity	NPC119562
0.82	Intermediate Similarity	NPC279410
0.82	Intermediate Similarity	NPC474922
0.8198	Intermediate Similarity	NPC157380
0.8182	Intermediate Similarity	NPC78594
0.8173	Intermediate Similarity	NPC470972
0.8173	Intermediate Similarity	NPC476081
0.8155	Intermediate Similarity	NPC473510
0.8155	Intermediate Similarity	NPC20113

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 NPC160583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1513
0.2-0.3	4046
0.3-0.4	2348
0.4-0.5	590
0.5-0.6	203
0.6-0.7	193
0.7-0.8	80
0.8-0.85	10
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.898	High Similarity	NPD7638	Approved
0.8889	High Similarity	NPD7639	Approved
0.8889	High Similarity	NPD7640	Approved
0.8796	High Similarity	NPD7328	Approved
0.8796	High Similarity	NPD7327	Approved
0.8716	High Similarity	NPD7516	Approved
0.8468	Intermediate Similarity	NPD8294	Approved
0.8468	Intermediate Similarity	NPD8377	Approved
0.8393	Intermediate Similarity	NPD8296	Approved
0.8393	Intermediate Similarity	NPD8379	Approved
0.8393	Intermediate Similarity	NPD8380	Approved
0.8393	Intermediate Similarity	NPD8335	Approved
0.8393	Intermediate Similarity	NPD8378	Approved
0.8393	Intermediate Similarity	NPD8033	Approved
0.8173	Intermediate Similarity	NPD7632	Discontinued
0.8103	Intermediate Similarity	NPD7507	Approved
0.7899	Intermediate Similarity	NPD7319	Approved
0.78	Intermediate Similarity	NPD6051	Approved
0.7798	Intermediate Similarity	NPD7320	Approved
0.7789	Intermediate Similarity	NPD7525	Registered
0.7778	Intermediate Similarity	NPD6675	Approved
0.7778	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD5739	Approved
0.7759	Intermediate Similarity	NPD7503	Approved
0.7636	Intermediate Similarity	NPD6881	Approved
0.7636	Intermediate Similarity	NPD6899	Approved
0.7615	Intermediate Similarity	NPD6008	Approved
0.7568	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD6373	Approved
0.7568	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5701	Approved
0.7545	Intermediate Similarity	NPD5697	Approved
0.7522	Intermediate Similarity	NPD6053	Discontinued
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7456	Intermediate Similarity	NPD4632	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7434	Intermediate Similarity	NPD6617	Approved
0.7434	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6649	Approved
0.7434	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD6869	Approved
0.7434	Intermediate Similarity	NPD8130	Phase 1
0.7434	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6013	Approved
0.7411	Intermediate Similarity	NPD6014	Approved
0.7411	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD4202	Approved
0.7368	Intermediate Similarity	NPD6882	Approved
0.7368	Intermediate Similarity	NPD8297	Approved
0.7345	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6686	Approved
0.729	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD7492	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7265	Intermediate Similarity	NPD6009	Approved
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD6399	Phase 3
0.7236	Intermediate Similarity	NPD7736	Approved
0.7227	Intermediate Similarity	NPD6319	Approved
0.7227	Intermediate Similarity	NPD6059	Approved
0.7227	Intermediate Similarity	NPD6054	Approved
0.7222	Intermediate Similarity	NPD4225	Approved
0.7213	Intermediate Similarity	NPD6616	Approved
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7184	Intermediate Similarity	NPD6903	Approved
0.7184	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5211	Phase 2
0.717	Intermediate Similarity	NPD7748	Approved
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7156	Intermediate Similarity	NPD5285	Approved
0.7156	Intermediate Similarity	NPD4700	Approved
0.7156	Intermediate Similarity	NPD5286	Approved
0.7156	Intermediate Similarity	NPD4696	Approved
0.7154	Intermediate Similarity	NPD7078	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD7902	Approved
0.7129	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5328	Approved
0.7107	Intermediate Similarity	NPD6370	Approved
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.7091	Intermediate Similarity	NPD5223	Approved
0.708	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7073	Intermediate Similarity	NPD6336	Discontinued
0.7064	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6335	Approved
0.7054	Intermediate Similarity	NPD5141	Approved
0.7034	Intermediate Similarity	NPD6274	Approved
0.703	Intermediate Similarity	NPD6695	Phase 3
0.7027	Intermediate Similarity	NPD5225	Approved
0.7027	Intermediate Similarity	NPD5224	Approved
0.7027	Intermediate Similarity	NPD4633	Approved
0.7027	Intermediate Similarity	NPD5226	Approved
0.7025	Intermediate Similarity	NPD6015	Approved
0.7025	Intermediate Similarity	NPD6016	Approved
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.699	Remote Similarity	NPD3618	Phase 1
0.6981	Remote Similarity	NPD6079	Approved
0.6981	Remote Similarity	NPD7637	Suspended
0.6975	Remote Similarity	NPD6317	Approved
0.697	Remote Similarity	NPD4195	Approved
0.6967	Remote Similarity	NPD5988	Approved
0.6964	Remote Similarity	NPD4754	Approved
0.6964	Remote Similarity	NPD5175	Approved
0.6964	Remote Similarity	NPD5174	Approved
0.6963	Remote Similarity	NPD7625	Phase 1
0.6961	Remote Similarity	NPD3665	Phase 1
0.6961	Remote Similarity	NPD3666	Approved
0.6961	Remote Similarity	NPD3133	Approved
0.6952	Remote Similarity	NPD4753	Phase 2
0.6952	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD6673	Approved
0.6952	Remote Similarity	NPD6080	Approved
0.6931	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6314	Approved
0.6907	Remote Similarity	NPD7339	Approved
0.6907	Remote Similarity	NPD6942	Approved
0.6897	Remote Similarity	NPD4634	Approved
0.6885	Remote Similarity	NPD6908	Approved
0.6885	Remote Similarity	NPD6909	Approved
0.6885	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6672	Approved
0.6857	Remote Similarity	NPD5737	Approved
0.6852	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7900	Approved
0.6852	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD4768	Approved
0.6842	Remote Similarity	NPD4767	Approved
0.6825	Remote Similarity	NPD6033	Approved
0.6822	Remote Similarity	NPD5281	Approved
0.6822	Remote Similarity	NPD5284	Approved
0.68	Remote Similarity	NPD7645	Phase 2
0.6796	Remote Similarity	NPD4786	Approved
0.6774	Remote Similarity	NPD6067	Discontinued
0.6771	Remote Similarity	NPD4243	Approved
0.6765	Remote Similarity	NPD4223	Phase 3
0.6765	Remote Similarity	NPD4221	Approved
0.6762	Remote Similarity	NPD7524	Approved
0.6762	Remote Similarity	NPD7750	Discontinued
0.6733	Remote Similarity	NPD6928	Phase 2
0.6733	Remote Similarity	NPD6930	Phase 2
0.6733	Remote Similarity	NPD6931	Approved
0.6731	Remote Similarity	NPD5329	Approved
0.6727	Remote Similarity	NPD5221	Approved
0.6727	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5222	Approved
0.6727	Remote Similarity	NPD4697	Phase 3
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4730	Approved
0.6724	Remote Similarity	NPD4729	Approved
0.6724	Remote Similarity	NPD5128	Approved
0.67	Remote Similarity	NPD6114	Approved
0.67	Remote Similarity	NPD6115	Approved
0.67	Remote Similarity	NPD6118	Approved
0.67	Remote Similarity	NPD6697	Approved
0.6699	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6636	Remote Similarity	NPD4629	Approved
0.6636	Remote Similarity	NPD5210	Approved
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4197	Approved
0.6634	Remote Similarity	NPD6929	Approved
0.6633	Remote Similarity	NPD6924	Approved
0.6633	Remote Similarity	NPD4784	Approved
0.6633	Remote Similarity	NPD4785	Approved
0.6633	Remote Similarity	NPD6926	Approved
0.6612	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD5248	Approved
0.661	Remote Similarity	NPD5250	Approved
0.661	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5169	Approved
0.661	Remote Similarity	NPD6371	Approved
0.661	Remote Similarity	NPD5247	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