NPASS Compound

Structure

NPC474585 OpenBabel07101719522D 33 38 0 0 1 0 0 0 0 0999 V2000 -4.1391 -0.4350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3427 1.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 0.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3066 1.7975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9873 1.8549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8371 2.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8371 1.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9936 2.7714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9936 -0.1505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1501 -0.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4632 1.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3803 0.8235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2607 -1.5902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7080 -1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4614 -0.2587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3512 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4530 1.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9936 0.8235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3066 0.8235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3066 -0.1505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1501 2.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6734 0.3138 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6650 1.6786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3803 -0.1505 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1501 1.3105 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7836 -0.0824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4632 -0.6375 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1041 -0.8022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3066 2.7714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7668 2.6472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0278 -1.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7752 1.2824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 27 1 1 0 0 0 21 25 1 0 0 0 0 21 29 2 0 0 0 0 22 15 1 1 0 0 0 22 26 1 0 0 0 0 22 32 1 0 0 0 0 23 30 2 0 0 0 0 23 32 1 0 0 0 0 24 27 1 6 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 26 33 1 0 0 0 0 27 13 1 1 0 0 0 27 33 1 0 0 0 0 28 24 1 6 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.26
Volume:	472.274
LogP:	3.266
LogD:	2.659
LogS:	-4.763
# Rotatable Bonds:	1
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	6.191
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.906
MDCK Permeability:	1.9932926079491153e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.883
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.969
Plasma Protein Binding (PPB):	86.43804168701172%
Volume Distribution (VD):	1.801
Pgp-substrate:	7.587798118591309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.801
CYP2C19-inhibitor:	0.834
CYP2C19-substrate:	0.885
CYP2C9-inhibitor:	0.61
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	9.638
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.821
Human Hepatotoxicity (H-HT):	0.886
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.927
Carcinogencity:	0.936
Eye Corrosion:	0.006
Eye Irritation:	0.02
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC474585

Natural Product ID:	NPC474585
*Common Name:**	Coagulin C
IUPAC Name:	n.a.
Synonyms:	Coagulin C
Standard InCHIKey:	SQIMTAKSNDBHOX-MEZCUPPISA-N
Standard InCHI:	InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6,8-9,19-20,22,31H,7,10-15H2,1-5H3/t19-,20+,22+,24-,25-,26-,27+,28-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@]1(C)O[C@]23[C@]([C@@]1(O)CC2)(C)CC[C@H]1[C@H]3CC=C2[C@]1(C)C(=O)C=CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL475326
PubChem CID:	44562952
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	=	22.8	%	PMID[458190]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	16.9	%	PMID[458190]

☑ 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 NPC474585 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	243
0.1-0.2	1275
0.2-0.3	4151
0.3-0.4	7564
0.4-0.5	13344
0.5-0.6	6741
0.6-0.7	6917
0.7-0.8	2301
0.8-0.85	111
0.85-0.9	30
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9818	High Similarity	NPC153440
0.973	High Similarity	NPC5292
0.9643	High Similarity	NPC79579
0.9636	High Similarity	NPC190286
0.9554	High Similarity	NPC270850
0.9554	High Similarity	NPC305260
0.9474	High Similarity	NPC107493
0.9386	High Similarity	NPC46570
0.9286	High Similarity	NPC176840
0.906	High Similarity	NPC473979
0.9027	High Similarity	NPC474181
0.8879	High Similarity	NPC475041
0.885	High Similarity	NPC236217
0.8824	High Similarity	NPC8369
0.8739	High Similarity	NPC469789
0.8689	High Similarity	NPC231529
0.8684	High Similarity	NPC191620
0.8678	High Similarity	NPC287423
0.8673	High Similarity	NPC37116
0.8673	High Similarity	NPC473627
0.8655	High Similarity	NPC170538
0.8655	High Similarity	NPC269642
0.8632	High Similarity	NPC475913
0.8595	High Similarity	NPC293112
0.8595	High Similarity	NPC473635
0.8583	High Similarity	NPC11895
0.8571	High Similarity	NPC67569
0.8559	High Similarity	NPC475520
0.8559	High Similarity	NPC474179
0.8559	High Similarity	NPC475834
0.8534	High Similarity	NPC326542
0.8522	High Similarity	NPC126691
0.8512	High Similarity	NPC81736
0.8512	High Similarity	NPC8374
0.8512	High Similarity	NPC172154
0.8509	High Similarity	NPC197428
0.85	High Similarity	NPC470265
0.85	High Similarity	NPC23786
0.8487	Intermediate Similarity	NPC474370
0.8475	Intermediate Similarity	NPC475372
0.8468	Intermediate Similarity	NPC173347
0.8462	Intermediate Similarity	NPC266728
0.8462	Intermediate Similarity	NPC49492
0.8455	Intermediate Similarity	NPC473888
0.8455	Intermediate Similarity	NPC311534
0.8455	Intermediate Similarity	NPC245094
0.8448	Intermediate Similarity	NPC194100
0.8448	Intermediate Similarity	NPC25909
0.8435	Intermediate Similarity	NPC470961
0.843	Intermediate Similarity	NPC120724
0.843	Intermediate Similarity	NPC204812
0.8417	Intermediate Similarity	NPC310511
0.8403	Intermediate Similarity	NPC312536
0.8403	Intermediate Similarity	NPC264954
0.84	Intermediate Similarity	NPC471855
0.839	Intermediate Similarity	NPC284068
0.8387	Intermediate Similarity	NPC473593
0.8378	Intermediate Similarity	NPC475320
0.8376	Intermediate Similarity	NPC471398
0.8376	Intermediate Similarity	NPC470953
0.8374	Intermediate Similarity	NPC473253
0.8374	Intermediate Similarity	NPC473265
0.8374	Intermediate Similarity	NPC470882
0.8362	Intermediate Similarity	NPC207251
0.8362	Intermediate Similarity	NPC269530
0.8361	Intermediate Similarity	NPC241456
0.8361	Intermediate Similarity	NPC32868
0.8348	Intermediate Similarity	NPC29133
0.8348	Intermediate Similarity	NPC5103
0.8348	Intermediate Similarity	NPC5284
0.8347	Intermediate Similarity	NPC222688
0.8347	Intermediate Similarity	NPC88326
0.8347	Intermediate Similarity	NPC153700
0.8346	Intermediate Similarity	NPC158350
0.8333	Intermediate Similarity	NPC143755
0.8333	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC472825
0.832	Intermediate Similarity	NPC213634
0.8319	Intermediate Similarity	NPC96377
0.8319	Intermediate Similarity	NPC311554
0.8319	Intermediate Similarity	NPC257457
0.8319	Intermediate Similarity	NPC186525
0.8319	Intermediate Similarity	NPC709
0.8319	Intermediate Similarity	NPC473720
0.8319	Intermediate Similarity	NPC50774
0.8306	Intermediate Similarity	NPC473620
0.8305	Intermediate Similarity	NPC148458
0.8305	Intermediate Similarity	NPC138372
0.8305	Intermediate Similarity	NPC106228
0.8305	Intermediate Similarity	NPC64318
0.8304	Intermediate Similarity	NPC474775
0.8293	Intermediate Similarity	NPC159499
0.8291	Intermediate Similarity	NPC469463
0.8291	Intermediate Similarity	NPC469454
0.8291	Intermediate Similarity	NPC250109
0.8291	Intermediate Similarity	NPC469496
0.8291	Intermediate Similarity	NPC471204
0.8291	Intermediate Similarity	NPC962
0.8279	Intermediate Similarity	NPC6193
0.8279	Intermediate Similarity	NPC27363
0.8276	Intermediate Similarity	NPC304180
0.8276	Intermediate Similarity	NPC179798
0.8264	Intermediate Similarity	NPC202051
0.8261	Intermediate Similarity	NPC5475
0.8261	Intermediate Similarity	NPC472216
0.8261	Intermediate Similarity	NPC173905
0.8261	Intermediate Similarity	NPC284828
0.8254	Intermediate Similarity	NPC155529
0.825	Intermediate Similarity	NPC473203
0.825	Intermediate Similarity	NPC476529
0.825	Intermediate Similarity	NPC61520
0.825	Intermediate Similarity	NPC230513
0.825	Intermediate Similarity	NPC475775
0.825	Intermediate Similarity	NPC42673
0.825	Intermediate Similarity	NPC472667
0.8246	Intermediate Similarity	NPC144459
0.824	Intermediate Similarity	NPC471407
0.824	Intermediate Similarity	NPC470880
0.824	Intermediate Similarity	NPC221414
0.8235	Intermediate Similarity	NPC20302
0.8235	Intermediate Similarity	NPC167606
0.8235	Intermediate Similarity	NPC473656
0.8235	Intermediate Similarity	NPC286528
0.8235	Intermediate Similarity	NPC239273
0.8235	Intermediate Similarity	NPC470492
0.8235	Intermediate Similarity	NPC473968
0.8235	Intermediate Similarity	NPC140055
0.823	Intermediate Similarity	NPC255309
0.8226	Intermediate Similarity	NPC42399
0.822	Intermediate Similarity	NPC147912
0.822	Intermediate Similarity	NPC67259
0.822	Intermediate Similarity	NPC178289
0.8214	Intermediate Similarity	NPC22388
0.8211	Intermediate Similarity	NPC473255
0.8205	Intermediate Similarity	NPC475524
0.8205	Intermediate Similarity	NPC470063
0.8205	Intermediate Similarity	NPC221144
0.8205	Intermediate Similarity	NPC234042
0.8205	Intermediate Similarity	NPC152117
0.8205	Intermediate Similarity	NPC100267
0.819	Intermediate Similarity	NPC41551
0.8182	Intermediate Similarity	NPC109607
0.8182	Intermediate Similarity	NPC107338
0.8182	Intermediate Similarity	NPC109973
0.8174	Intermediate Similarity	NPC189075
0.8174	Intermediate Similarity	NPC65941
0.8174	Intermediate Similarity	NPC275539
0.8167	Intermediate Similarity	NPC329736
0.8158	Intermediate Similarity	NPC323834
0.8151	Intermediate Similarity	NPC476963
0.8151	Intermediate Similarity	NPC196931
0.8145	Intermediate Similarity	NPC469750
0.8145	Intermediate Similarity	NPC250556
0.8142	Intermediate Similarity	NPC140723
0.814	Intermediate Similarity	NPC130447
0.814	Intermediate Similarity	NPC245017
0.8136	Intermediate Similarity	NPC317210
0.8136	Intermediate Similarity	NPC178981
0.8136	Intermediate Similarity	NPC56448
0.8136	Intermediate Similarity	NPC255017
0.8125	Intermediate Similarity	NPC296617
0.8125	Intermediate Similarity	NPC471234
0.812	Intermediate Similarity	NPC470076
0.8115	Intermediate Similarity	NPC204731
0.8103	Intermediate Similarity	NPC41405
0.8103	Intermediate Similarity	NPC469370
0.8099	Intermediate Similarity	NPC9674
0.8099	Intermediate Similarity	NPC19028
0.8099	Intermediate Similarity	NPC473636
0.8099	Intermediate Similarity	NPC476960
0.8099	Intermediate Similarity	NPC77689
0.8099	Intermediate Similarity	NPC278681
0.8095	Intermediate Similarity	NPC476966
0.8095	Intermediate Similarity	NPC175186
0.8095	Intermediate Similarity	NPC104382
0.8087	Intermediate Similarity	NPC91034
0.8087	Intermediate Similarity	NPC110496
0.8087	Intermediate Similarity	NPC59530
0.8087	Intermediate Similarity	NPC475294
0.8083	Intermediate Similarity	NPC476959
0.8083	Intermediate Similarity	NPC134430
0.8083	Intermediate Similarity	NPC312824
0.8083	Intermediate Similarity	NPC476965
0.8083	Intermediate Similarity	NPC469684
0.8083	Intermediate Similarity	NPC470959
0.8083	Intermediate Similarity	NPC470493
0.8083	Intermediate Similarity	NPC471854
0.8083	Intermediate Similarity	NPC23046
0.8083	Intermediate Similarity	NPC183580
0.808	Intermediate Similarity	NPC240070
0.808	Intermediate Similarity	NPC469757
0.808	Intermediate Similarity	NPC117702
0.808	Intermediate Similarity	NPC471357
0.808	Intermediate Similarity	NPC179412
0.808	Intermediate Similarity	NPC329784
0.808	Intermediate Similarity	NPC146456
0.808	Intermediate Similarity	NPC471356
0.807	Intermediate Similarity	NPC228669
0.807	Intermediate Similarity	NPC471293
0.807	Intermediate Similarity	NPC164835

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 NPC474585 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1499
0.2-0.3	3755
0.3-0.4	2413
0.4-0.5	766
0.5-0.6	233
0.6-0.7	179
0.7-0.8	94
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7115	Discovery
0.8205	Intermediate Similarity	NPD6053	Discontinued
0.8145	Intermediate Similarity	NPD7507	Approved
0.8136	Intermediate Similarity	NPD4632	Approved
0.8065	Intermediate Similarity	NPD7492	Approved
0.8051	Intermediate Similarity	NPD8297	Approved
0.8033	Intermediate Similarity	NPD6319	Approved
0.8033	Intermediate Similarity	NPD6054	Approved
0.8017	Intermediate Similarity	NPD6881	Approved
0.8017	Intermediate Similarity	NPD6899	Approved
0.8016	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD6008	Approved
0.7953	Intermediate Similarity	NPD7319	Approved
0.7937	Intermediate Similarity	NPD7078	Approved
0.7931	Intermediate Similarity	NPD5697	Approved
0.7903	Intermediate Similarity	NPD6370	Approved
0.7881	Intermediate Similarity	NPD7102	Approved
0.7881	Intermediate Similarity	NPD7290	Approved
0.7881	Intermediate Similarity	NPD6883	Approved
0.7863	Intermediate Similarity	NPD7320	Approved
0.7845	Intermediate Similarity	NPD5739	Approved
0.7845	Intermediate Similarity	NPD7128	Approved
0.7845	Intermediate Similarity	NPD6675	Approved
0.7845	Intermediate Similarity	NPD6402	Approved
0.7823	Intermediate Similarity	NPD6016	Approved
0.7823	Intermediate Similarity	NPD7503	Approved
0.7823	Intermediate Similarity	NPD6015	Approved
0.7815	Intermediate Similarity	NPD6649	Approved
0.7815	Intermediate Similarity	NPD8130	Phase 1
0.7815	Intermediate Similarity	NPD6869	Approved
0.7815	Intermediate Similarity	NPD6847	Approved
0.7815	Intermediate Similarity	NPD6650	Approved
0.7815	Intermediate Similarity	NPD6617	Approved
0.7797	Intermediate Similarity	NPD6013	Approved
0.7797	Intermediate Similarity	NPD6012	Approved
0.7797	Intermediate Similarity	NPD6014	Approved
0.7787	Intermediate Similarity	NPD6009	Approved
0.776	Intermediate Similarity	NPD5988	Approved
0.775	Intermediate Similarity	NPD6882	Approved
0.7742	Intermediate Similarity	NPD6059	Approved
0.7712	Intermediate Similarity	NPD6011	Approved
0.7698	Intermediate Similarity	NPD7604	Phase 2
0.768	Intermediate Similarity	NPD5983	Phase 2
0.768	Intermediate Similarity	NPD8033	Approved
0.7656	Intermediate Similarity	NPD8293	Discontinued
0.7647	Intermediate Similarity	NPD6372	Approved
0.7647	Intermediate Similarity	NPD6373	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.7627	Intermediate Similarity	NPD5701	Approved
0.7627	Intermediate Similarity	NPD6412	Phase 2
0.7586	Intermediate Similarity	NPD5211	Phase 2
0.7583	Intermediate Similarity	NPD4634	Approved
0.7581	Intermediate Similarity	NPD7328	Approved
0.7581	Intermediate Similarity	NPD7327	Approved
0.7578	Intermediate Similarity	NPD6336	Discontinued
0.7565	Intermediate Similarity	NPD5285	Approved
0.7565	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD7639	Approved
0.7565	Intermediate Similarity	NPD5286	Approved
0.7565	Intermediate Similarity	NPD4696	Approved
0.7522	Intermediate Similarity	NPD5695	Phase 3
0.752	Intermediate Similarity	NPD7516	Approved
0.746	Intermediate Similarity	NPD8294	Approved
0.746	Intermediate Similarity	NPD8377	Approved
0.7458	Intermediate Similarity	NPD5141	Approved
0.7436	Intermediate Similarity	NPD5224	Approved
0.7436	Intermediate Similarity	NPD5226	Approved
0.7436	Intermediate Similarity	NPD4633	Approved
0.7436	Intermediate Similarity	NPD5225	Approved
0.7417	Intermediate Similarity	NPD6686	Approved
0.7402	Intermediate Similarity	NPD8380	Approved
0.7402	Intermediate Similarity	NPD8335	Approved
0.7402	Intermediate Similarity	NPD8378	Approved
0.7402	Intermediate Similarity	NPD8379	Approved
0.7402	Intermediate Similarity	NPD8296	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD6084	Phase 2
0.7391	Intermediate Similarity	NPD6083	Phase 2
0.7381	Intermediate Similarity	NPD7101	Approved
0.7381	Intermediate Similarity	NPD7100	Approved
0.7377	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5175	Approved
0.7373	Intermediate Similarity	NPD5174	Approved
0.7368	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6335	Approved
0.7295	Intermediate Similarity	NPD6371	Approved
0.7293	Intermediate Similarity	NPD7260	Phase 2
0.728	Intermediate Similarity	NPD6274	Approved
0.7266	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4700	Approved
0.7257	Intermediate Similarity	NPD5281	Approved
0.7257	Intermediate Similarity	NPD6079	Approved
0.7257	Intermediate Similarity	NPD5284	Approved
0.7222	Intermediate Similarity	NPD6317	Approved
0.7197	Intermediate Similarity	NPD6033	Approved
0.7193	Intermediate Similarity	NPD6399	Phase 3
0.7179	Intermediate Similarity	NPD5696	Approved
0.7179	Intermediate Similarity	NPD4225	Approved
0.7168	Intermediate Similarity	NPD5207	Approved
0.7165	Intermediate Similarity	NPD6313	Approved
0.7165	Intermediate Similarity	NPD6314	Approved
0.7154	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7131	Intermediate Similarity	NPD4729	Approved
0.7131	Intermediate Similarity	NPD4730	Approved
0.7131	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7146	Approved
0.7117	Intermediate Similarity	NPD6684	Approved
0.7117	Intermediate Similarity	NPD7334	Approved
0.7117	Intermediate Similarity	NPD7521	Approved
0.7117	Intermediate Similarity	NPD6409	Approved
0.7117	Intermediate Similarity	NPD5330	Approved
0.7111	Intermediate Similarity	NPD6845	Suspended
0.7105	Intermediate Similarity	NPD5693	Phase 1
0.708	Intermediate Similarity	NPD5328	Approved
0.7043	Intermediate Similarity	NPD4202	Approved
0.7027	Intermediate Similarity	NPD1694	Approved
0.7016	Intermediate Similarity	NPD5249	Phase 3
0.7016	Intermediate Similarity	NPD5250	Approved
0.7016	Intermediate Similarity	NPD5251	Approved
0.7016	Intermediate Similarity	NPD5247	Approved
0.7016	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5221	Approved
0.7009	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD6909	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6992	Remote Similarity	NPD5128	Approved
0.6984	Remote Similarity	NPD8133	Approved
0.6983	Remote Similarity	NPD7748	Approved
0.6983	Remote Similarity	NPD6001	Approved
0.6967	Remote Similarity	NPD4768	Approved
0.6967	Remote Similarity	NPD4767	Approved
0.6964	Remote Similarity	NPD5690	Phase 2
0.696	Remote Similarity	NPD5216	Approved
0.696	Remote Similarity	NPD5217	Approved
0.696	Remote Similarity	NPD5215	Approved
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6949	Remote Similarity	NPD5173	Approved
0.6949	Remote Similarity	NPD7902	Approved
0.6942	Remote Similarity	NPD4754	Approved
0.693	Remote Similarity	NPD4753	Phase 2
0.693	Remote Similarity	NPD6673	Approved
0.693	Remote Similarity	NPD6080	Approved
0.693	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD4629	Approved
0.6917	Remote Similarity	NPD5344	Discontinued
0.6911	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3573	Approved
0.6897	Remote Similarity	NPD5779	Approved
0.6897	Remote Similarity	NPD5778	Approved
0.6894	Remote Similarity	NPD8328	Phase 3
0.6894	Remote Similarity	NPD6067	Discontinued
0.688	Remote Similarity	NPD5135	Approved
0.688	Remote Similarity	NPD5169	Approved
0.688	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6868	Approved
0.687	Remote Similarity	NPD5785	Approved
0.687	Remote Similarity	NPD46	Approved
0.687	Remote Similarity	NPD5692	Phase 3
0.687	Remote Similarity	NPD6698	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)
0.6825	Remote Similarity	NPD5127	Approved
0.681	Remote Similarity	NPD6411	Approved
0.681	Remote Similarity	NPD7515	Phase 2
0.68	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3666	Approved
0.6786	Remote Similarity	NPD3133	Approved
0.6786	Remote Similarity	NPD3665	Phase 1
0.6783	Remote Similarity	NPD6051	Approved
0.6757	Remote Similarity	NPD4221	Approved
0.6757	Remote Similarity	NPD4223	Phase 3
0.6757	Remote Similarity	NPD6435	Approved
0.6754	Remote Similarity	NPD4251	Approved
0.6754	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD7236	Approved
0.6726	Remote Similarity	NPD5329	Approved
0.6723	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5208	Approved
0.6695	Remote Similarity	NPD7900	Approved
0.6695	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD3574	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