NPASS Compound

Structure

CID152808 OpenBabel06191715522D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.7256 0.3001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4034 0.1243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2004 -1.8131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5332 0.4515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2412 -2.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5226 -1.6373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2209 1.4618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6888 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7344 -1.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3771 2.9243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6889 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5137 -0.2721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4122 -1.2408 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5332 2.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2209 2.4368 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6888 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 2.4369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 1.4619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5332 1.4619 0.0000 C 0 0 2 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 -0.8447 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0960 2.9419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0306 2.9421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5628 -0.5049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2725 -2.2496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 12 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 3 1 1 0 0 0 18 26 1 0 0 0 0 19 29 1 1 0 0 0 20 24 1 0 0 0 0 20 26 1 1 0 0 0 21 24 1 0 0 0 0 21 27 1 1 0 0 0 22 24 1 0 0 0 0 22 30 1 6 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.36
Volume:	491.143
LogP:	4.407
LogD:	4.051
LogS:	-4.374
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	5.007
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	1.201006853079889e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.14

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	94.04210662841797%
Volume Distribution (VD):	0.841
Pgp-substrate:	3.237955331802368%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.485
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.772
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	10.731
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.449
Skin Sensitization:	0.297
Carcinogencity:	0.626
Eye Corrosion:	0.035
Eye Irritation:	0.03
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC152808

Natural Product ID:	NPC152808
*Common Name:**	(20S)-5-Ergostene-3Beta,7Alpha,16Beta,20-Tetrol
IUPAC Name:	(3S,7S,8S,9S,10R,13S,14S,16S,17R)-17-[(2S,5R)-2-hydroxy-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7,16-triol
Synonyms:
Standard InCHIKey:	NAPNLPVMHUZNFG-BHTYWNIDSA-N
Standard InCHI:	InChI=1S/C28H48O4/c1-16(2)17(3)7-12-28(6,32)25-23(31)15-21-24-20(9-11-27(21,25)5)26(4)10-8-19(29)13-18(26)14-22(24)30/h14,16-17,19-25,29-32H,7-13,15H2,1-6H3/t17-,19+,20+,21+,22-,23+,24-,25+,26+,27+,28+/m1/s1
SMILES:	O[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]2([C@H]3C[C@@H]([C@@H]2[C@](CC[C@H](C(C)C)C)(O)C)O)C)O)C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641928
PubChem CID:	44191679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	9.4	ug.mL-1	PMID[509351]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	47.4	ug.mL-1	PMID[509351]

☑ 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 NPC152808 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	170
0.1-0.2	1385
0.2-0.3	5128
0.3-0.4	14909
0.4-0.5	8579
0.5-0.6	5994
0.6-0.7	4881
0.7-0.8	1365
0.8-0.85	177
0.85-0.9	77
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC293287
0.9512	High Similarity	NPC6391
0.9375	High Similarity	NPC209620
0.9375	High Similarity	NPC23852
0.9277	High Similarity	NPC261266
0.9268	High Similarity	NPC205845
0.9259	High Similarity	NPC470614
0.9259	High Similarity	NPC50964
0.9259	High Similarity	NPC1272
0.9259	High Similarity	NPC101462
0.925	High Similarity	NPC26117
0.9146	High Similarity	NPC474634
0.9136	High Similarity	NPC264245
0.9125	High Similarity	NPC109546
0.9125	High Similarity	NPC84694
0.9125	High Similarity	NPC143182
0.9125	High Similarity	NPC28862
0.9125	High Similarity	NPC47982
0.9125	High Similarity	NPC81306
0.9059	High Similarity	NPC474668
0.9036	High Similarity	NPC185568
0.9036	High Similarity	NPC124172
0.9024	High Similarity	NPC49964
0.9012	High Similarity	NPC164840
0.9012	High Similarity	NPC234193
0.9012	High Similarity	NPC241290
0.9012	High Similarity	NPC209944
0.9	High Similarity	NPC477522
0.9	High Similarity	NPC87604
0.9	High Similarity	NPC474216
0.8966	High Similarity	NPC97404
0.8966	High Similarity	NPC41554
0.8953	High Similarity	NPC470361
0.8941	High Similarity	NPC149224
0.8929	High Similarity	NPC318390
0.8929	High Similarity	NPC470360
0.8929	High Similarity	NPC266511
0.8916	High Similarity	NPC475789
0.8902	High Similarity	NPC47761
0.8902	High Similarity	NPC470383
0.8889	High Similarity	NPC209430
0.8889	High Similarity	NPC30986
0.8875	High Similarity	NPC318495
0.8875	High Similarity	NPC155986
0.8875	High Similarity	NPC198968
0.8851	High Similarity	NPC11216
0.8851	High Similarity	NPC291484
0.8851	High Similarity	NPC204188
0.8851	High Similarity	NPC3345
0.8851	High Similarity	NPC329596
0.8851	High Similarity	NPC80561
0.8851	High Similarity	NPC295668
0.8824	High Similarity	NPC139724
0.8824	High Similarity	NPC24277
0.8824	High Similarity	NPC299068
0.8824	High Similarity	NPC201273
0.881	High Similarity	NPC209802
0.8795	High Similarity	NPC189972
0.8765	High Similarity	NPC477514
0.8765	High Similarity	NPC473943
0.875	High Similarity	NPC244488
0.875	High Similarity	NPC321381
0.875	High Similarity	NPC96319
0.875	High Similarity	NPC247325
0.875	High Similarity	NPC321016
0.875	High Similarity	NPC107059
0.8706	High Similarity	NPC474349
0.8706	High Similarity	NPC474189
0.8706	High Similarity	NPC274448
0.869	High Similarity	NPC317458
0.869	High Similarity	NPC110778
0.8675	High Similarity	NPC474683
0.8675	High Similarity	NPC474731
0.8675	High Similarity	NPC474752
0.8675	High Similarity	NPC7505
0.8675	High Similarity	NPC82986
0.8675	High Similarity	NPC474759
0.8675	High Similarity	NPC320525
0.8659	High Similarity	NPC328714
0.8659	High Similarity	NPC1319
0.8625	High Similarity	NPC230301
0.8625	High Similarity	NPC304309
0.8625	High Similarity	NPC285893
0.8625	High Similarity	NPC288035
0.8625	High Similarity	NPC134847
0.8625	High Similarity	NPC136188
0.8625	High Similarity	NPC22105
0.8625	High Similarity	NPC162742
0.8625	High Similarity	NPC28657
0.8621	High Similarity	NPC470542
0.8621	High Similarity	NPC2158
0.8621	High Similarity	NPC133588
0.8605	High Similarity	NPC6605
0.8588	High Similarity	NPC475798
0.8588	High Similarity	NPC127606
0.8588	High Similarity	NPC238485
0.8588	High Similarity	NPC474047
0.8571	High Similarity	NPC30166
0.8571	High Similarity	NPC87489
0.8571	High Similarity	NPC288970
0.8571	High Similarity	NPC296701
0.8571	High Similarity	NPC218616
0.8556	High Similarity	NPC477605
0.8554	High Similarity	NPC324772
0.8523	High Similarity	NPC105495
0.8519	High Similarity	NPC300324
0.8519	High Similarity	NPC240604
0.8519	High Similarity	NPC113733
0.8506	High Similarity	NPC271967
0.8506	High Similarity	NPC475313
0.8488	Intermediate Similarity	NPC157257
0.8471	Intermediate Similarity	NPC470384
0.8471	Intermediate Similarity	NPC193870
0.8471	Intermediate Similarity	NPC477818
0.8471	Intermediate Similarity	NPC141941
0.8471	Intermediate Similarity	NPC232023
0.8471	Intermediate Similarity	NPC320548
0.8452	Intermediate Similarity	NPC476646
0.8452	Intermediate Similarity	NPC249423
0.8444	Intermediate Similarity	NPC310013
0.8444	Intermediate Similarity	NPC98193
0.8434	Intermediate Similarity	NPC476316
0.8427	Intermediate Similarity	NPC470390
0.8427	Intermediate Similarity	NPC473956
0.8427	Intermediate Similarity	NPC270511
0.8427	Intermediate Similarity	NPC245410
0.8427	Intermediate Similarity	NPC14380
0.8427	Intermediate Similarity	NPC192437
0.8427	Intermediate Similarity	NPC475751
0.8415	Intermediate Similarity	NPC34019
0.8409	Intermediate Similarity	NPC475664
0.8409	Intermediate Similarity	NPC67872
0.8409	Intermediate Similarity	NPC471952
0.8409	Intermediate Similarity	NPC280556
0.8395	Intermediate Similarity	NPC471723
0.8395	Intermediate Similarity	NPC141071
0.8395	Intermediate Similarity	NPC257347
0.8391	Intermediate Similarity	NPC94462
0.8372	Intermediate Similarity	NPC470077
0.8372	Intermediate Similarity	NPC256567
0.8372	Intermediate Similarity	NPC231310
0.8353	Intermediate Similarity	NPC470049
0.8353	Intermediate Similarity	NPC248886
0.8353	Intermediate Similarity	NPC201852
0.8353	Intermediate Similarity	NPC202389
0.8352	Intermediate Similarity	NPC279410
0.8352	Intermediate Similarity	NPC144202
0.8352	Intermediate Similarity	NPC65402
0.8352	Intermediate Similarity	NPC127718
0.8352	Intermediate Similarity	NPC119562
0.8333	Intermediate Similarity	NPC47149
0.8333	Intermediate Similarity	NPC322313
0.8333	Intermediate Similarity	NPC71535
0.8333	Intermediate Similarity	NPC275671
0.8333	Intermediate Similarity	NPC236237
0.8333	Intermediate Similarity	NPC234335
0.8333	Intermediate Similarity	NPC102253
0.8333	Intermediate Similarity	NPC78545
0.8333	Intermediate Similarity	NPC96362
0.8315	Intermediate Similarity	NPC101886
0.8315	Intermediate Similarity	NPC477606
0.8315	Intermediate Similarity	NPC109744
0.8315	Intermediate Similarity	NPC2983
0.8313	Intermediate Similarity	NPC83351
0.8313	Intermediate Similarity	NPC76931
0.8313	Intermediate Similarity	NPC472499
0.8313	Intermediate Similarity	NPC275910
0.8313	Intermediate Similarity	NPC167891
0.8313	Intermediate Similarity	NPC285761
0.8313	Intermediate Similarity	NPC472501
0.8313	Intermediate Similarity	NPC307965
0.8313	Intermediate Similarity	NPC18603
0.8313	Intermediate Similarity	NPC472500
0.8298	Intermediate Similarity	NPC154072
0.8295	Intermediate Similarity	NPC474657
0.8295	Intermediate Similarity	NPC470620
0.8295	Intermediate Similarity	NPC186145
0.8293	Intermediate Similarity	NPC189883
0.8293	Intermediate Similarity	NPC129165
0.8293	Intermediate Similarity	NPC253190
0.8293	Intermediate Similarity	NPC134330
0.828	Intermediate Similarity	NPC476893
0.828	Intermediate Similarity	NPC477226
0.8272	Intermediate Similarity	NPC469533
0.8272	Intermediate Similarity	NPC469534
0.8272	Intermediate Similarity	NPC306727
0.8272	Intermediate Similarity	NPC471797
0.8272	Intermediate Similarity	NPC469593
0.8261	Intermediate Similarity	NPC8774
0.8256	Intermediate Similarity	NPC82623
0.8256	Intermediate Similarity	NPC113978
0.8247	Intermediate Similarity	NPC257353
0.8242	Intermediate Similarity	NPC472942
0.8242	Intermediate Similarity	NPC27531
0.8235	Intermediate Similarity	NPC157655
0.8235	Intermediate Similarity	NPC474531
0.8222	Intermediate Similarity	NPC107189
0.8222	Intermediate Similarity	NPC320026
0.8214	Intermediate Similarity	NPC472463
0.8214	Intermediate Similarity	NPC24504

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 NPC152808 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	1592
0.2-0.3	4212
0.3-0.4	2257
0.4-0.5	480
0.5-0.6	170
0.6-0.7	176
0.7-0.8	86
0.8-0.85	17
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD4751	Clinical (unspecified phase)
0.875	High Similarity	NPD3701	Clinical (unspecified phase)
0.8625	High Similarity	NPD6942	Approved
0.8625	High Similarity	NPD7339	Approved
0.8554	High Similarity	NPD6930	Phase 2
0.8554	High Similarity	NPD6931	Approved
0.8471	Intermediate Similarity	NPD6695	Phase 3
0.8434	Intermediate Similarity	NPD6929	Approved
0.8372	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7525	Registered
0.8333	Intermediate Similarity	NPD7514	Phase 3
0.8272	Intermediate Similarity	NPD4784	Approved
0.8272	Intermediate Similarity	NPD4785	Approved
0.825	Intermediate Similarity	NPD4243	Approved
0.8193	Intermediate Similarity	NPD6925	Approved
0.8193	Intermediate Similarity	NPD5776	Phase 2
0.8118	Intermediate Similarity	NPD7332	Phase 2
0.8095	Intermediate Similarity	NPD7145	Approved
0.809	Intermediate Similarity	NPD7750	Discontinued
0.809	Intermediate Similarity	NPD7524	Approved
0.8068	Intermediate Similarity	NPD6893	Approved
0.8049	Intermediate Similarity	NPD6926	Approved
0.8049	Intermediate Similarity	NPD6924	Approved
0.8023	Intermediate Similarity	NPD6902	Approved
0.7976	Intermediate Similarity	NPD6932	Approved
0.7955	Intermediate Similarity	NPD4786	Approved
0.7907	Intermediate Similarity	NPD4748	Discontinued
0.7857	Intermediate Similarity	NPD6933	Approved
0.7816	Intermediate Similarity	NPD6898	Phase 1
0.7791	Intermediate Similarity	NPD6683	Phase 2
0.7742	Intermediate Similarity	NPD7087	Discontinued
0.7738	Intermediate Similarity	NPD4190	Phase 3
0.7738	Intermediate Similarity	NPD5275	Approved
0.7727	Intermediate Similarity	NPD3667	Approved
0.7717	Intermediate Similarity	NPD4753	Phase 2
0.7674	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7152	Approved
0.759	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD7151	Approved
0.7586	Intermediate Similarity	NPD4195	Approved
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7561	Intermediate Similarity	NPD6923	Approved
0.7561	Intermediate Similarity	NPD6922	Approved
0.7556	Intermediate Similarity	NPD3665	Phase 1
0.7556	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD3133	Approved
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.7527	Intermediate Similarity	NPD6051	Approved
0.7526	Intermediate Similarity	NPD4755	Approved
0.7474	Intermediate Similarity	NPD4202	Approved
0.747	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7426	Intermediate Similarity	NPD5141	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7368	Intermediate Similarity	NPD7637	Suspended
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD4223	Phase 3
0.7326	Intermediate Similarity	NPD8264	Approved
0.732	Intermediate Similarity	NPD5210	Approved
0.732	Intermediate Similarity	NPD4629	Approved
0.7303	Intermediate Similarity	NPD7509	Discontinued
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7283	Intermediate Similarity	NPD5329	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.7188	Intermediate Similarity	NPD6079	Approved
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7174	Intermediate Similarity	NPD4197	Approved
0.7174	Intermediate Similarity	NPD3668	Phase 3
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD7136	Phase 2
0.7075	Intermediate Similarity	NPD4634	Approved
0.7065	Intermediate Similarity	NPD4788	Approved
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7021	Intermediate Similarity	NPD4693	Phase 3
0.7021	Intermediate Similarity	NPD4690	Approved
0.7021	Intermediate Similarity	NPD4138	Approved
0.7021	Intermediate Similarity	NPD4688	Approved
0.7021	Intermediate Similarity	NPD5205	Approved
0.7021	Intermediate Similarity	NPD4689	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.7019	Intermediate Similarity	NPD4767	Approved
0.699	Remote Similarity	NPD4754	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.697	Remote Similarity	NPD5695	Phase 3
0.6961	Remote Similarity	NPD4159	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6952	Remote Similarity	NPD6412	Phase 2
0.6941	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7327	Approved
0.6937	Remote Similarity	NPD7328	Approved
0.6931	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD7632	Discontinued
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD4723	Approved
0.6875	Remote Similarity	NPD7516	Approved
0.6875	Remote Similarity	NPD4722	Approved
0.686	Remote Similarity	NPD4787	Phase 1
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5280	Approved
0.6842	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD4694	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD5173	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6814	Remote Similarity	NPD8377	Approved
0.6814	Remote Similarity	NPD8294	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6789	Remote Similarity	NPD6053	Discontinued
0.6759	Remote Similarity	NPD5249	Phase 3
0.6759	Remote Similarity	NPD5247	Approved
0.6759	Remote Similarity	NPD5250	Approved
0.6759	Remote Similarity	NPD5251	Approved
0.6759	Remote Similarity	NPD5248	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6754	Remote Similarity	NPD8379	Approved
0.6754	Remote Similarity	NPD8378	Approved
0.6754	Remote Similarity	NPD8296	Approved
0.6754	Remote Similarity	NPD8380	Approved
0.6754	Remote Similarity	NPD8335	Approved
0.6737	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6011	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6707	Remote Similarity	NPD368	Approved
0.6703	Remote Similarity	NPD4271	Approved
0.6703	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD5362	Discontinued
0.6702	Remote Similarity	NPD5332	Approved
0.6701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6697	Remote Similarity	NPD5217	Approved
0.6697	Remote Similarity	NPD5215	Approved
0.6697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD6904	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