NPASS Compound

Structure

CID329596 OpenBabel06191716212D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.8145 3.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2759 3.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3023 5.5845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8924 4.7419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5346 3.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8408 4.7413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3535 3.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2222 2.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 2.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3018 3.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8149 4.7410 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3793 3.8981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6894 0.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 2.9239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5340 1.4620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8450 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5343 2.4366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9752 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 2.5541 -0.4993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 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 18 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 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 14 1 0 0 0 0 11 20 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 27 1 0 0 0 0 15 21 2 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 29 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 6 0 0 0 23 26 1 6 0 0 0 24 27 1 6 0 0 0 25 28 1 6 0 0 0 25 30 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 6 0 0 0 28 31 1 1 0 0 0 M END

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	479.716
LogP:	5.237
LogD:	5.07
LogS:	-5.355
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	4.926
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.771
MDCK Permeability:	5.187620627111755e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.163
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.48

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	91.65406799316406%
Volume Distribution (VD):	1.068
Pgp-substrate:	1.8574049472808838%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.401
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.847
CYP2C9-inhibitor:	0.248
CYP2C9-substrate:	0.136
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.643

ADMET: Excretion

Clearance (CL):	1.774
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.034
Carcinogencity:	0.004
Eye Corrosion:	0.004
Eye Irritation:	0.077
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC329596

Natural Product ID:	NPC329596
*Common Name:**	Ergosta-7,22-Diene-3B,5A,6B-Triol
IUPAC Name:	(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
Synonyms:
Standard InCHIKey:	ARXHRTZAVQOQEU-PHZYAEJDSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+/t18?,19-,20+,22-,23+,24+,25-,26-,27-,28+/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@@](C1)(O)[C@H](O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/C(C(C)C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL263108
PubChem CID:	12302766
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
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.666	uM	PMID[520789]

☑ 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 NPC329596 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	179
0.1-0.2	1367
0.2-0.3	4811
0.3-0.4	12677
0.4-0.5	10767
0.5-0.6	5994
0.6-0.7	5011
0.7-0.8	1548
0.8-0.85	231
0.85-0.9	83
0.9-0.95	17
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80561
1.0	High Similarity	NPC3345
1.0	High Similarity	NPC204188
1.0	High Similarity	NPC291484
1.0	High Similarity	NPC11216
0.9882	High Similarity	NPC41554
0.9882	High Similarity	NPC97404
0.9881	High Similarity	NPC470361
0.954	High Similarity	NPC310013
0.9529	High Similarity	NPC133588
0.9524	High Similarity	NPC299068
0.9438	High Similarity	NPC288970
0.9432	High Similarity	NPC127718
0.9432	High Similarity	NPC65402
0.9405	High Similarity	NPC470360
0.9326	High Similarity	NPC8774
0.9302	High Similarity	NPC474668
0.9294	High Similarity	NPC261266
0.9294	High Similarity	NPC6391
0.9222	High Similarity	NPC98457
0.9222	High Similarity	NPC227583
0.9222	High Similarity	NPC12103
0.9121	High Similarity	NPC261807
0.9091	High Similarity	NPC470390
0.9091	High Similarity	NPC270511
0.9091	High Similarity	NPC245410
0.9091	High Similarity	NPC192437
0.9091	High Similarity	NPC14380
0.9059	High Similarity	NPC185568
0.9059	High Similarity	NPC205845
0.9048	High Similarity	NPC49964
0.9048	High Similarity	NPC50964
0.9011	High Similarity	NPC210717
0.9011	High Similarity	NPC103165
0.8989	High Similarity	NPC275671
0.8977	High Similarity	NPC101886
0.8941	High Similarity	NPC317458
0.8941	High Similarity	NPC474634
0.8929	High Similarity	NPC264245
0.8929	High Similarity	NPC476646
0.8929	High Similarity	NPC23852
0.8929	High Similarity	NPC470383
0.8929	High Similarity	NPC209620
0.8929	High Similarity	NPC249423
0.8876	High Similarity	NPC473956
0.8876	High Similarity	NPC475751
0.8876	High Similarity	NPC295668
0.8864	High Similarity	NPC67872
0.8864	High Similarity	NPC4574
0.8864	High Similarity	NPC212596
0.8851	High Similarity	NPC152808
0.8851	High Similarity	NPC293287
0.8851	High Similarity	NPC94462
0.8824	High Similarity	NPC87489
0.8824	High Similarity	NPC30166
0.8824	High Similarity	NPC296701
0.8824	High Similarity	NPC218616
0.8824	High Similarity	NPC101462
0.881	High Similarity	NPC164840
0.881	High Similarity	NPC241290
0.881	High Similarity	NPC209944
0.881	High Similarity	NPC234193
0.881	High Similarity	NPC96362
0.8791	High Similarity	NPC144202
0.8791	High Similarity	NPC477605
0.8764	High Similarity	NPC109744
0.8764	High Similarity	NPC138974
0.875	High Similarity	NPC149224
0.875	High Similarity	NPC470620
0.875	High Similarity	NPC304083
0.8736	High Similarity	NPC274448
0.871	High Similarity	NPC477226
0.871	High Similarity	NPC476893
0.8706	High Similarity	NPC474531
0.8706	High Similarity	NPC47761
0.869	High Similarity	NPC143182
0.869	High Similarity	NPC28862
0.869	High Similarity	NPC328714
0.869	High Similarity	NPC81306
0.869	High Similarity	NPC84694
0.869	High Similarity	NPC109546
0.869	High Similarity	NPC30986
0.869	High Similarity	NPC47982
0.869	High Similarity	NPC209430
0.8681	High Similarity	NPC137461
0.8681	High Similarity	NPC27531
0.8652	High Similarity	NPC475605
0.8652	High Similarity	NPC475664
0.8652	High Similarity	NPC280556
0.8636	High Similarity	NPC71520
0.8636	High Similarity	NPC6605
0.8636	High Similarity	NPC269058
0.8636	High Similarity	NPC201273
0.8636	High Similarity	NPC139724
0.8621	High Similarity	NPC231310
0.8621	High Similarity	NPC238485
0.8621	High Similarity	NPC470077
0.8621	High Similarity	NPC124172
0.8617	High Similarity	NPC476895
0.8602	High Similarity	NPC72204
0.8588	High Similarity	NPC236112
0.8588	High Similarity	NPC287749
0.8588	High Similarity	NPC13554
0.8571	High Similarity	NPC210268
0.8571	High Similarity	NPC83351
0.8571	High Similarity	NPC474216
0.8571	High Similarity	NPC87604
0.8571	High Similarity	NPC114389
0.8571	High Similarity	NPC167891
0.8556	High Similarity	NPC105495
0.8556	High Similarity	NPC187785
0.8556	High Similarity	NPC259875
0.8539	High Similarity	NPC474657
0.8539	High Similarity	NPC186145
0.8523	High Similarity	NPC318390
0.8523	High Similarity	NPC157257
0.8523	High Similarity	NPC266511
0.8506	High Similarity	NPC320548
0.8506	High Similarity	NPC211135
0.8506	High Similarity	NPC216420
0.8506	High Similarity	NPC113978
0.8506	High Similarity	NPC475789
0.8506	High Similarity	NPC470384
0.8506	High Similarity	NPC207013
0.8506	High Similarity	NPC82623
0.8506	High Similarity	NPC85095
0.8506	High Similarity	NPC477818
0.8495	Intermediate Similarity	NPC476894
0.8485	Intermediate Similarity	NPC472218
0.8485	Intermediate Similarity	NPC472217
0.8485	Intermediate Similarity	NPC472219
0.8471	Intermediate Similarity	NPC80530
0.8471	Intermediate Similarity	NPC273410
0.8452	Intermediate Similarity	NPC91594
0.8452	Intermediate Similarity	NPC155986
0.8452	Intermediate Similarity	NPC471798
0.8452	Intermediate Similarity	NPC198968
0.8452	Intermediate Similarity	NPC130136
0.8452	Intermediate Similarity	NPC318495
0.8438	Intermediate Similarity	NPC476896
0.8427	Intermediate Similarity	NPC24277
0.8427	Intermediate Similarity	NPC121981
0.8427	Intermediate Similarity	NPC125399
0.8409	Intermediate Similarity	NPC474493
0.8409	Intermediate Similarity	NPC474047
0.8409	Intermediate Similarity	NPC475798
0.8409	Intermediate Similarity	NPC209802
0.8409	Intermediate Similarity	NPC127606
0.8409	Intermediate Similarity	NPC15534
0.8404	Intermediate Similarity	NPC471903
0.8391	Intermediate Similarity	NPC470049
0.8391	Intermediate Similarity	NPC189972
0.8391	Intermediate Similarity	NPC248886
0.8391	Intermediate Similarity	NPC470614
0.8391	Intermediate Similarity	NPC1272
0.8391	Intermediate Similarity	NPC202389
0.8391	Intermediate Similarity	NPC7988
0.8372	Intermediate Similarity	NPC322313
0.8372	Intermediate Similarity	NPC236237
0.8372	Intermediate Similarity	NPC102253
0.8372	Intermediate Similarity	NPC324772
0.8372	Intermediate Similarity	NPC26117
0.8353	Intermediate Similarity	NPC167037
0.8353	Intermediate Similarity	NPC244385
0.8353	Intermediate Similarity	NPC138621
0.8353	Intermediate Similarity	NPC31828
0.8353	Intermediate Similarity	NPC285761
0.8353	Intermediate Similarity	NPC6978
0.8353	Intermediate Similarity	NPC275910
0.8353	Intermediate Similarity	NPC473943
0.8352	Intermediate Similarity	NPC477606
0.8333	Intermediate Similarity	NPC129165
0.8333	Intermediate Similarity	NPC240604
0.8333	Intermediate Similarity	NPC475313
0.8333	Intermediate Similarity	NPC321016
0.8333	Intermediate Similarity	NPC107059
0.8333	Intermediate Similarity	NPC244488
0.8333	Intermediate Similarity	NPC300324
0.8333	Intermediate Similarity	NPC189883
0.8333	Intermediate Similarity	NPC253190
0.8333	Intermediate Similarity	NPC134330
0.8333	Intermediate Similarity	NPC247325
0.8333	Intermediate Similarity	NPC113733
0.8333	Intermediate Similarity	NPC265588
0.8333	Intermediate Similarity	NPC321381
0.8295	Intermediate Similarity	NPC141941
0.8295	Intermediate Similarity	NPC134481
0.8295	Intermediate Similarity	NPC470558
0.8295	Intermediate Similarity	NPC110778
0.8295	Intermediate Similarity	NPC193870
0.8295	Intermediate Similarity	NPC232023
0.8283	Intermediate Similarity	NPC166607
0.828	Intermediate Similarity	NPC98193
0.828	Intermediate Similarity	NPC119379
0.8276	Intermediate Similarity	NPC474752
0.8276	Intermediate Similarity	NPC7505
0.8276	Intermediate Similarity	NPC471270
0.8276	Intermediate Similarity	NPC320525
0.8276	Intermediate Similarity	NPC474731
0.8276	Intermediate Similarity	NPC474683

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 NPC329596 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1553
0.2-0.3	4148
0.3-0.4	2207
0.4-0.5	616
0.5-0.6	196
0.6-0.7	169
0.7-0.8	68
0.8-0.85	16
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD7525	Registered
0.8372	Intermediate Similarity	NPD7514	Phase 3
0.8372	Intermediate Similarity	NPD6930	Phase 2
0.8372	Intermediate Similarity	NPD6931	Approved
0.8333	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD6929	Approved
0.8214	Intermediate Similarity	NPD7339	Approved
0.8214	Intermediate Similarity	NPD6942	Approved
0.8202	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7332	Phase 2
0.814	Intermediate Similarity	NPD7145	Approved
0.8132	Intermediate Similarity	NPD7524	Approved
0.809	Intermediate Similarity	NPD6695	Phase 3
0.8068	Intermediate Similarity	NPD6902	Approved
0.8023	Intermediate Similarity	NPD5776	Phase 2
0.8023	Intermediate Similarity	NPD6932	Approved
0.8023	Intermediate Similarity	NPD6925	Approved
0.7912	Intermediate Similarity	NPD6893	Approved
0.7907	Intermediate Similarity	NPD6933	Approved
0.7907	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7750	Discontinued
0.7674	Intermediate Similarity	NPD4785	Approved
0.7674	Intermediate Similarity	NPD4784	Approved
0.7674	Intermediate Similarity	NPD6924	Approved
0.7674	Intermediate Similarity	NPD6926	Approved
0.7667	Intermediate Similarity	NPD6898	Phase 1
0.764	Intermediate Similarity	NPD7645	Phase 2
0.764	Intermediate Similarity	NPD6683	Phase 2
0.7609	Intermediate Similarity	NPD4786	Approved
0.7528	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5211	Phase 2
0.7442	Intermediate Similarity	NPD4243	Approved
0.7442	Intermediate Similarity	NPD7150	Approved
0.7442	Intermediate Similarity	NPD7151	Approved
0.7442	Intermediate Similarity	NPD7152	Approved
0.7423	Intermediate Similarity	NPD7087	Discontinued
0.7423	Intermediate Similarity	NPD6079	Approved
0.7396	Intermediate Similarity	NPD5328	Approved
0.7391	Intermediate Similarity	NPD3667	Approved
0.7386	Intermediate Similarity	NPD8264	Approved
0.7363	Intermediate Similarity	NPD7509	Discontinued
0.7363	Intermediate Similarity	NPD4748	Discontinued
0.7347	Intermediate Similarity	NPD4202	Approved
0.7326	Intermediate Similarity	NPD7143	Approved
0.7326	Intermediate Similarity	NPD7144	Approved
0.7308	Intermediate Similarity	NPD5141	Approved
0.729	Intermediate Similarity	NPD4634	Approved
0.7263	Intermediate Similarity	NPD3618	Phase 1
0.7255	Intermediate Similarity	NPD7640	Approved
0.7255	Intermediate Similarity	NPD7639	Approved
0.7255	Intermediate Similarity	NPD5286	Approved
0.7255	Intermediate Similarity	NPD4696	Approved
0.7255	Intermediate Similarity	NPD5285	Approved
0.7245	Intermediate Similarity	NPD7637	Suspended
0.7228	Intermediate Similarity	NPD4755	Approved
0.7209	Intermediate Similarity	NPD6922	Approved
0.7209	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6923	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7184	Intermediate Similarity	NPD4159	Approved
0.7157	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7115	Intermediate Similarity	NPD5225	Approved
0.7115	Intermediate Similarity	NPD4633	Approved
0.7115	Intermediate Similarity	NPD5224	Approved
0.7115	Intermediate Similarity	NPD5226	Approved
0.7087	Intermediate Similarity	NPD4700	Approved
0.708	Intermediate Similarity	NPD7516	Approved
0.7065	Intermediate Similarity	NPD4195	Approved
0.7048	Intermediate Similarity	NPD5175	Approved
0.7048	Intermediate Similarity	NPD5174	Approved
0.7019	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD5275	Approved
0.7	Intermediate Similarity	NPD4190	Phase 3
0.7	Intermediate Similarity	NPD6399	Phase 3
0.697	Remote Similarity	NPD7136	Phase 2
0.6961	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5222	Approved
0.6961	Remote Similarity	NPD5221	Approved
0.6957	Remote Similarity	NPD8335	Approved
0.6957	Remote Similarity	NPD8380	Approved
0.6957	Remote Similarity	NPD8033	Approved
0.6957	Remote Similarity	NPD7503	Approved
0.6957	Remote Similarity	NPD8379	Approved
0.6957	Remote Similarity	NPD8296	Approved
0.6957	Remote Similarity	NPD8378	Approved
0.6944	Remote Similarity	NPD6881	Approved
0.6944	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD4632	Approved
0.6916	Remote Similarity	NPD7128	Approved
0.6916	Remote Similarity	NPD5739	Approved
0.6916	Remote Similarity	NPD6675	Approved
0.6916	Remote Similarity	NPD6402	Approved
0.6893	Remote Similarity	NPD5173	Approved
0.6875	Remote Similarity	NPD3666	Approved
0.6875	Remote Similarity	NPD3133	Approved
0.6875	Remote Similarity	NPD3665	Phase 1
0.687	Remote Similarity	NPD8377	Approved
0.687	Remote Similarity	NPD8294	Approved
0.6869	Remote Similarity	NPD4753	Phase 2
0.6857	Remote Similarity	NPD5344	Discontinued
0.6852	Remote Similarity	NPD5697	Approved
0.6847	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD4225	Approved
0.6818	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD7290	Approved
0.6804	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4697	Phase 3
0.6789	Remote Similarity	NPD4730	Approved
0.6789	Remote Similarity	NPD4729	Approved
0.6789	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD368	Approved
0.6759	Remote Similarity	NPD4768	Approved
0.6759	Remote Similarity	NPD4767	Approved
0.6757	Remote Similarity	NPD6617	Approved
0.6757	Remote Similarity	NPD6869	Approved
0.6757	Remote Similarity	NPD6649	Approved
0.6757	Remote Similarity	NPD6847	Approved
0.6757	Remote Similarity	NPD6650	Approved
0.6757	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD4754	Approved
0.6727	Remote Similarity	NPD6014	Approved
0.6727	Remote Similarity	NPD6373	Approved
0.6727	Remote Similarity	NPD6372	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6013	Approved
0.6727	Remote Similarity	NPD6012	Approved
0.6724	Remote Similarity	NPD6054	Approved
0.6724	Remote Similarity	NPD6319	Approved
0.6701	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD6051	Approved
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6697	Remote Similarity	NPD6412	Phase 2
0.6697	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6636	Remote Similarity	NPD6011	Approved
0.6633	Remote Similarity	NPD5329	Approved
0.661	Remote Similarity	NPD6370	Approved
0.6609	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD5217	Approved
0.6607	Remote Similarity	NPD5216	Approved
0.6606	Remote Similarity	NPD6640	Phase 3
0.6593	Remote Similarity	NPD4732	Discontinued
0.6583	Remote Similarity	NPD7507	Approved
0.6581	Remote Similarity	NPD6059	Approved
0.6571	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD6083	Phase 2
0.6569	Remote Similarity	NPD7515	Phase 2
0.6566	Remote Similarity	NPD5279	Phase 3
0.6566	Remote Similarity	NPD4519	Discontinued
0.6566	Remote Similarity	NPD4623	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6531	Remote Similarity	NPD4197	Approved
0.6525	Remote Similarity	NPD6015	Approved
0.6525	Remote Similarity	NPD6016	Approved
0.6518	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD5169	Approved
0.6518	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7492	Approved
0.6471	Remote Similarity	NPD5988	Approved
0.646	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6455	Remote Similarity	NPD6008	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6446	Remote Similarity	NPD6616	Approved
0.6441	Remote Similarity	NPD7741	Discontinued
0.6429	Remote Similarity	NPD4788	Approved
0.6417	Remote Similarity	NPD7604	Phase 2
0.6408	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD8035	Phase 2
0.64	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4689	Approved
0.64	Remote Similarity	NPD4693	Phase 3
0.64	Remote Similarity	NPD5205	Approved
0.64	Remote Similarity	NPD5690	Phase 2
0.64	Remote Similarity	NPD4688	Approved
0.64	Remote Similarity	NPD4138	Approved
0.64	Remote Similarity	NPD4690	Approved
0.6393	Remote Similarity	NPD7078	Approved
0.6387	Remote Similarity	NPD5983	Phase 2
0.6374	Remote Similarity	NPD4787	Phase 1
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)

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