NPASS Compound

Structure

NPC79579 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 5.0826 2.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4984 0.7421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0032 2.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -1.7321 1.0000 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 3.3884 2.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3395 2.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5474 1.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6453 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8042 0.3820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6942 1.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0121 -0.5962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0251 2.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 2.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 0.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 24 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 15 16 2 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 28 1 6 0 0 0 20 25 1 0 0 0 0 20 29 2 0 0 0 0 21 28 1 6 0 0 0 21 30 1 0 0 0 0 22 26 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 35 1 0 0 0 0 24 27 1 6 0 0 0 25 4 1 1 0 0 0 26 5 1 6 0 0 0 26 27 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 1 0 0 0 28 24 1 6 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.26
Volume:	498.411
LogP:	2.262
LogD:	1.56
LogS:	-4.214
# Rotatable Bonds:	2
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	5.573
Fsp3:	0.714
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:	-4.871
MDCK Permeability:	2.063832107523922e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.261
20% Bioavailability (F20%):	0.302
30% Bioavailability (F30%):	0.551

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	82.77700805664062%
Volume Distribution (VD):	0.906
Pgp-substrate:	14.200345993041992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.796
CYP3A4-substrate:	0.841

ADMET: Excretion

Clearance (CL):	3.09
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.343
Human Hepatotoxicity (H-HT):	0.591
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.911
Carcinogencity:	0.971
Eye Corrosion:	0.004
Eye Irritation:	0.015
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: NPC79579

Natural Product ID:	NPC79579
*Common Name:**	Coagulanolide
IUPAC Name:	(2R)-2-[(1S)-1-hydroxy-1-[(8R,9S,10R,13S,14R,15S,17S)-14,15,17-trihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:	coagulanolide
Standard InCHIKey:	XAEUKOBJPRGERY-VLXOZLMASA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-15-13-22(35-23(31)16(15)2)26(5,32)27(33)14-21(30)28(34)19-10-9-17-7-6-8-20(29)25(17,4)18(19)11-12-24(27,28)3/h6,8-9,18-19,21-22,30,32-34H,7,10-14H2,1-5H3/t18-,19+,21-,22+,24+,25-,26-,27-,28-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@@]1(C[C@@H]([C@]2([C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520391
PubChem CID:	44562997
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	Species	Solanaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	28.1	%	PMID[550360]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	14.7	%	PMID[550360]

☑ 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 NPC79579 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	237
0.1-0.2	1283
0.2-0.3	3988
0.3-0.4	7142
0.4-0.5	13120
0.5-0.6	6823
0.6-0.7	7080
0.7-0.8	2758
0.8-0.85	204
0.85-0.9	39
0.9-0.95	8
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC153440
0.973	High Similarity	NPC5292
0.9646	High Similarity	NPC107493
0.9643	High Similarity	NPC474585
0.9636	High Similarity	NPC190286
0.9558	High Similarity	NPC46570
0.9554	High Similarity	NPC270850
0.9554	High Similarity	NPC305260
0.9286	High Similarity	NPC176840
0.906	High Similarity	NPC473979
0.9043	High Similarity	NPC475041
0.9018	High Similarity	NPC236217
0.8898	High Similarity	NPC469789
0.886	High Similarity	NPC474181
0.885	High Similarity	NPC191620
0.8839	High Similarity	NPC37116
0.8814	High Similarity	NPC269642
0.875	High Similarity	NPC293112
0.8739	High Similarity	NPC11895
0.8729	High Similarity	NPC67569
0.8689	High Similarity	NPC231529
0.8673	High Similarity	NPC473627
0.8673	High Similarity	NPC197428
0.8667	High Similarity	NPC81736
0.8667	High Similarity	NPC8369
0.8667	High Similarity	NPC172154
0.8667	High Similarity	NPC8374
0.8661	High Similarity	NPC472825
0.8655	High Similarity	NPC170538
0.8655	High Similarity	NPC470265
0.8655	High Similarity	NPC23786
0.8644	High Similarity	NPC474370
0.8618	High Similarity	NPC173347
0.8609	High Similarity	NPC194100
0.8607	High Similarity	NPC245094
0.8596	High Similarity	NPC470961
0.8595	High Similarity	NPC473635
0.8595	High Similarity	NPC159499
0.8559	High Similarity	NPC264954
0.8548	High Similarity	NPC471855
0.8534	High Similarity	NPC470953
0.8525	High Similarity	NPC473265
0.8525	High Similarity	NPC287423
0.8522	High Similarity	NPC126691
0.8509	High Similarity	NPC41551
0.8509	High Similarity	NPC29133
0.85	High Similarity	NPC153700
0.85	High Similarity	NPC88326
0.8492	Intermediate Similarity	NPC158350
0.8487	Intermediate Similarity	NPC476961
0.8475	Intermediate Similarity	NPC257457
0.8475	Intermediate Similarity	NPC311554
0.8475	Intermediate Similarity	NPC475913
0.8475	Intermediate Similarity	NPC186525
0.8475	Intermediate Similarity	NPC50774
0.8475	Intermediate Similarity	NPC709
0.8468	Intermediate Similarity	NPC213634
0.8462	Intermediate Similarity	NPC148458
0.8462	Intermediate Similarity	NPC64318
0.8455	Intermediate Similarity	NPC311534
0.8448	Intermediate Similarity	NPC962
0.8448	Intermediate Similarity	NPC25909
0.8448	Intermediate Similarity	NPC250109
0.843	Intermediate Similarity	NPC6193
0.843	Intermediate Similarity	NPC204812
0.8421	Intermediate Similarity	NPC284828
0.8421	Intermediate Similarity	NPC472216
0.8421	Intermediate Similarity	NPC173905
0.8421	Intermediate Similarity	NPC5475
0.8417	Intermediate Similarity	NPC202051
0.8417	Intermediate Similarity	NPC310511
0.8407	Intermediate Similarity	NPC144459
0.8403	Intermediate Similarity	NPC474179
0.8403	Intermediate Similarity	NPC278681
0.8403	Intermediate Similarity	NPC61520
0.8403	Intermediate Similarity	NPC473203
0.8403	Intermediate Similarity	NPC475834
0.84	Intermediate Similarity	NPC155529
0.839	Intermediate Similarity	NPC140055
0.839	Intermediate Similarity	NPC239273
0.839	Intermediate Similarity	NPC20302
0.839	Intermediate Similarity	NPC286528
0.839	Intermediate Similarity	NPC470492
0.839	Intermediate Similarity	NPC167606
0.8387	Intermediate Similarity	NPC470880
0.8387	Intermediate Similarity	NPC471407
0.8387	Intermediate Similarity	NPC221414
0.8378	Intermediate Similarity	NPC475320
0.8376	Intermediate Similarity	NPC326542
0.8376	Intermediate Similarity	NPC67259
0.8376	Intermediate Similarity	NPC147912
0.8374	Intermediate Similarity	NPC473253
0.8374	Intermediate Similarity	NPC470882
0.8362	Intermediate Similarity	NPC152117
0.8362	Intermediate Similarity	NPC221144
0.8362	Intermediate Similarity	NPC475524
0.8362	Intermediate Similarity	NPC234042
0.8362	Intermediate Similarity	NPC100267
0.8361	Intermediate Similarity	NPC241456
0.8361	Intermediate Similarity	NPC473255
0.8361	Intermediate Similarity	NPC32868
0.8348	Intermediate Similarity	NPC5103
0.8348	Intermediate Similarity	NPC50223
0.8333	Intermediate Similarity	NPC112936
0.8333	Intermediate Similarity	NPC65941
0.8319	Intermediate Similarity	NPC16701
0.8319	Intermediate Similarity	NPC323834
0.8319	Intermediate Similarity	NPC329736
0.8306	Intermediate Similarity	NPC473888
0.8305	Intermediate Similarity	NPC49492
0.8305	Intermediate Similarity	NPC298278
0.8305	Intermediate Similarity	NPC476963
0.8305	Intermediate Similarity	NPC266728
0.8291	Intermediate Similarity	NPC469463
0.8291	Intermediate Similarity	NPC255017
0.8291	Intermediate Similarity	NPC317210
0.8291	Intermediate Similarity	NPC469496
0.8291	Intermediate Similarity	NPC469454
0.8291	Intermediate Similarity	NPC471204
0.8279	Intermediate Similarity	NPC27363
0.8279	Intermediate Similarity	NPC120724
0.8276	Intermediate Similarity	NPC470076
0.8261	Intermediate Similarity	NPC41405
0.825	Intermediate Similarity	NPC213761
0.825	Intermediate Similarity	NPC77689
0.825	Intermediate Similarity	NPC35171
0.825	Intermediate Similarity	NPC476960
0.825	Intermediate Similarity	NPC475520
0.825	Intermediate Similarity	NPC475775
0.825	Intermediate Similarity	NPC473636
0.825	Intermediate Similarity	NPC476529
0.825	Intermediate Similarity	NPC472667
0.8246	Intermediate Similarity	NPC475294
0.8246	Intermediate Similarity	NPC91034
0.824	Intermediate Similarity	NPC473593
0.824	Intermediate Similarity	NPC476966
0.8235	Intermediate Similarity	NPC157380
0.8235	Intermediate Similarity	NPC134430
0.8235	Intermediate Similarity	NPC476959
0.8235	Intermediate Similarity	NPC470959
0.8235	Intermediate Similarity	NPC470493
0.8235	Intermediate Similarity	NPC185287
0.8235	Intermediate Similarity	NPC183580
0.8235	Intermediate Similarity	NPC471854
0.8235	Intermediate Similarity	NPC473968
0.8235	Intermediate Similarity	NPC284068
0.8235	Intermediate Similarity	NPC476965
0.8235	Intermediate Similarity	NPC312824
0.822	Intermediate Similarity	NPC471398
0.822	Intermediate Similarity	NPC305044
0.822	Intermediate Similarity	NPC178289
0.822	Intermediate Similarity	NPC265290
0.822	Intermediate Similarity	NPC473898
0.8214	Intermediate Similarity	NPC22388
0.8214	Intermediate Similarity	NPC473424
0.8211	Intermediate Similarity	NPC469790
0.8205	Intermediate Similarity	NPC277769
0.8205	Intermediate Similarity	NPC470063
0.8205	Intermediate Similarity	NPC269530
0.8205	Intermediate Similarity	NPC207251
0.8197	Intermediate Similarity	NPC222688
0.819	Intermediate Similarity	NPC5284
0.8182	Intermediate Similarity	NPC109607
0.8182	Intermediate Similarity	NPC476962
0.8182	Intermediate Similarity	NPC251226
0.8182	Intermediate Similarity	NPC107338
0.8182	Intermediate Similarity	NPC145074
0.8182	Intermediate Similarity	NPC114939
0.8182	Intermediate Similarity	NPC41123
0.8182	Intermediate Similarity	NPC268530
0.8182	Intermediate Similarity	NPC154491
0.8174	Intermediate Similarity	NPC472218
0.8174	Intermediate Similarity	NPC472217
0.8174	Intermediate Similarity	NPC472219
0.8174	Intermediate Similarity	NPC177064
0.8174	Intermediate Similarity	NPC329417
0.8174	Intermediate Similarity	NPC189075
0.8174	Intermediate Similarity	NPC275539
0.8167	Intermediate Similarity	NPC475372
0.816	Intermediate Similarity	NPC473620
0.8158	Intermediate Similarity	NPC96377
0.8158	Intermediate Similarity	NPC60681
0.8158	Intermediate Similarity	NPC231530
0.8158	Intermediate Similarity	NPC278628
0.8154	Intermediate Similarity	NPC75616
0.8151	Intermediate Similarity	NPC106228
0.8151	Intermediate Similarity	NPC270929
0.8151	Intermediate Similarity	NPC138372
0.8151	Intermediate Similarity	NPC196931
0.8145	Intermediate Similarity	NPC469750
0.8145	Intermediate Similarity	NPC250556
0.8142	Intermediate Similarity	NPC474775
0.8142	Intermediate Similarity	NPC236390
0.814	Intermediate Similarity	NPC130447
0.814	Intermediate Similarity	NPC245017
0.814	Intermediate Similarity	NPC127656
0.8136	Intermediate Similarity	NPC122056
0.8136	Intermediate Similarity	NPC101400
0.8136	Intermediate Similarity	NPC178981
0.8136	Intermediate Similarity	NPC101965

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 NPC79579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1507
0.2-0.3	3654
0.3-0.4	2420
0.4-0.5	833
0.5-0.6	253
0.6-0.7	155
0.7-0.8	117
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.839	Intermediate Similarity	NPD7115	Discovery
0.8333	Intermediate Similarity	NPD6319	Approved
0.8291	Intermediate Similarity	NPD4632	Approved
0.8205	Intermediate Similarity	NPD8297	Approved
0.8205	Intermediate Similarity	NPD6053	Discontinued
0.8174	Intermediate Similarity	NPD6899	Approved
0.8174	Intermediate Similarity	NPD6881	Approved
0.8145	Intermediate Similarity	NPD7507	Approved
0.8087	Intermediate Similarity	NPD5697	Approved
0.8065	Intermediate Similarity	NPD7492	Approved
0.8034	Intermediate Similarity	NPD7102	Approved
0.8034	Intermediate Similarity	NPD7290	Approved
0.8034	Intermediate Similarity	NPD6883	Approved
0.8033	Intermediate Similarity	NPD6054	Approved
0.8016	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7967	Intermediate Similarity	NPD7503	Approved
0.7966	Intermediate Similarity	NPD6869	Approved
0.7966	Intermediate Similarity	NPD8130	Phase 1
0.7966	Intermediate Similarity	NPD6617	Approved
0.7966	Intermediate Similarity	NPD6649	Approved
0.7966	Intermediate Similarity	NPD6847	Approved
0.7966	Intermediate Similarity	NPD6650	Approved
0.7953	Intermediate Similarity	NPD7319	Approved
0.7949	Intermediate Similarity	NPD6014	Approved
0.7949	Intermediate Similarity	NPD6013	Approved
0.7949	Intermediate Similarity	NPD6012	Approved
0.7937	Intermediate Similarity	NPD7078	Approved
0.7934	Intermediate Similarity	NPD6009	Approved
0.7903	Intermediate Similarity	NPD6370	Approved
0.7899	Intermediate Similarity	NPD6882	Approved
0.7881	Intermediate Similarity	NPD4634	Approved
0.7863	Intermediate Similarity	NPD7320	Approved
0.7863	Intermediate Similarity	NPD6011	Approved
0.784	Intermediate Similarity	NPD7604	Phase 2
0.7823	Intermediate Similarity	NPD6016	Approved
0.7823	Intermediate Similarity	NPD5983	Phase 2
0.7823	Intermediate Similarity	NPD6015	Approved
0.7797	Intermediate Similarity	NPD6373	Approved
0.7797	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7778	Intermediate Similarity	NPD5701	Approved
0.776	Intermediate Similarity	NPD5988	Approved
0.7742	Intermediate Similarity	NPD6059	Approved
0.7739	Intermediate Similarity	NPD5211	Phase 2
0.7719	Intermediate Similarity	NPD5286	Approved
0.7719	Intermediate Similarity	NPD7640	Approved
0.7719	Intermediate Similarity	NPD4696	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7719	Intermediate Similarity	NPD5285	Approved
0.7717	Intermediate Similarity	NPD6336	Discontinued
0.7692	Intermediate Similarity	NPD6008	Approved
0.768	Intermediate Similarity	NPD8033	Approved
0.7656	Intermediate Similarity	NPD8293	Discontinued
0.7607	Intermediate Similarity	NPD5141	Approved
0.7586	Intermediate Similarity	NPD5226	Approved
0.7586	Intermediate Similarity	NPD5225	Approved
0.7586	Intermediate Similarity	NPD4633	Approved
0.7586	Intermediate Similarity	NPD5224	Approved
0.7581	Intermediate Similarity	NPD7328	Approved
0.7581	Intermediate Similarity	NPD7327	Approved
0.7563	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD6083	Phase 2
0.7544	Intermediate Similarity	NPD4755	Approved
0.7544	Intermediate Similarity	NPD6084	Phase 2
0.7522	Intermediate Similarity	NPD5695	Phase 3
0.7521	Intermediate Similarity	NPD5175	Approved
0.7521	Intermediate Similarity	NPD5174	Approved
0.7521	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7101	Approved
0.752	Intermediate Similarity	NPD7100	Approved
0.752	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD8294	Approved
0.746	Intermediate Similarity	NPD8377	Approved
0.744	Intermediate Similarity	NPD6335	Approved
0.7438	Intermediate Similarity	NPD6371	Approved
0.7419	Intermediate Similarity	NPD6274	Approved
0.7414	Intermediate Similarity	NPD4700	Approved
0.7411	Intermediate Similarity	NPD6079	Approved
0.7402	Intermediate Similarity	NPD8380	Approved
0.7402	Intermediate Similarity	NPD8378	Approved
0.7402	Intermediate Similarity	NPD8379	Approved
0.7402	Intermediate Similarity	NPD8296	Approved
0.7402	Intermediate Similarity	NPD8335	Approved
0.736	Intermediate Similarity	NPD6317	Approved
0.7302	Intermediate Similarity	NPD6313	Approved
0.7302	Intermediate Similarity	NPD6314	Approved
0.7293	Intermediate Similarity	NPD7260	Phase 2
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD5281	Approved
0.7257	Intermediate Similarity	NPD5284	Approved
0.7232	Intermediate Similarity	NPD5328	Approved
0.7197	Intermediate Similarity	NPD6033	Approved
0.7193	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD4202	Approved
0.7179	Intermediate Similarity	NPD5696	Approved
0.7179	Intermediate Similarity	NPD4225	Approved
0.7155	Intermediate Similarity	NPD5221	Approved
0.7155	Intermediate Similarity	NPD5222	Approved
0.7155	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5249	Phase 3
0.7154	Intermediate Similarity	NPD5247	Approved
0.7154	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5251	Approved
0.7154	Intermediate Similarity	NPD5250	Approved
0.7154	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7132	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6908	Approved
0.7132	Intermediate Similarity	NPD6909	Approved
0.7131	Intermediate Similarity	NPD5128	Approved
0.712	Intermediate Similarity	NPD8133	Approved
0.7117	Intermediate Similarity	NPD7146	Approved
0.7117	Intermediate Similarity	NPD6684	Approved
0.7117	Intermediate Similarity	NPD7521	Approved
0.7117	Intermediate Similarity	NPD7334	Approved
0.7117	Intermediate Similarity	NPD6409	Approved
0.7117	Intermediate Similarity	NPD5330	Approved
0.7107	Intermediate Similarity	NPD4767	Approved
0.7107	Intermediate Similarity	NPD4768	Approved
0.7105	Intermediate Similarity	NPD5693	Phase 1
0.7097	Intermediate Similarity	NPD5215	Approved
0.7097	Intermediate Similarity	NPD5217	Approved
0.7097	Intermediate Similarity	NPD5216	Approved
0.7094	Intermediate Similarity	NPD5173	Approved
0.7083	Intermediate Similarity	NPD4754	Approved
0.708	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD5210	Approved
0.7069	Intermediate Similarity	NPD4629	Approved
0.7069	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5344	Discontinued
0.7049	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5778	Approved
0.7043	Intermediate Similarity	NPD5779	Approved
0.7023	Intermediate Similarity	NPD8328	Phase 3
0.7018	Intermediate Similarity	NPD46	Approved
0.7018	Intermediate Similarity	NPD6698	Approved
0.7018	Intermediate Similarity	NPD5785	Approved
0.7016	Intermediate Similarity	NPD5169	Approved
0.7016	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5135	Approved
0.7008	Intermediate Similarity	NPD6868	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6991	Remote Similarity	NPD6903	Approved
0.6983	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD5690	Phase 2
0.696	Remote Similarity	NPD5127	Approved
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6957	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD6411	Approved
0.6949	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD3133	Approved
0.6937	Remote Similarity	NPD3666	Approved
0.6937	Remote Similarity	NPD3665	Phase 1
0.6935	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6673	Approved
0.693	Remote Similarity	NPD6904	Approved
0.693	Remote Similarity	NPD6080	Approved
0.6911	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6435	Approved
0.6903	Remote Similarity	NPD3573	Approved
0.6894	Remote Similarity	NPD6067	Discontinued
0.6875	Remote Similarity	NPD1694	Approved
0.687	Remote Similarity	NPD5207	Approved
0.687	Remote Similarity	NPD5692	Phase 3
0.6864	Remote Similarity	NPD4697	Phase 3
0.6861	Remote Similarity	NPD6845	Suspended
0.6849	Remote Similarity	NPD7236	Approved
0.6846	Remote Similarity	NPD4522	Approved
0.6842	Remote Similarity	NPD5737	Approved
0.6842	Remote Similarity	NPD6672	Approved
0.6838	Remote Similarity	NPD5956	Approved
0.6825	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3618	Phase 1
0.6797	Remote Similarity	NPD5167	Approved
0.6786	Remote Similarity	NPD4786	Approved
0.6783	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6101	Approved
0.6783	Remote Similarity	NPD6051	Approved
0.678	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4221	Approved
0.6757	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD5368	Approved
0.6726	Remote Similarity	NPD5329	Approved
0.6724	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD5208	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