NPASS Compound

Structure

NPC475243 OpenBabel07101718282D 52 56 0 0 1 0 0 0 0 0999 V2000 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3989 -0.8316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4478 -1.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7321 -6.0000 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 1.8605 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 -0.4898 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 -0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6776 0.0454 0.0000 C 0 0 2 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 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3904 1.2044 0.0000 C 0 0 1 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 -4.6557 -0.1625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0814 2.1554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3249 0.5806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -5.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3686 0.9965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 5 36 1 0 0 0 0 6 36 1 0 0 0 0 9 39 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 39 1 0 0 0 0 17 26 1 0 0 0 0 17 30 1 0 0 0 0 18 27 1 0 0 0 0 18 38 1 0 0 0 0 19 31 1 0 0 0 0 19 37 1 0 0 0 0 20 32 1 0 0 0 0 20 37 1 0 0 0 0 21 41 2 0 0 0 0 21 49 1 0 0 0 0 22 42 2 0 0 0 0 22 50 1 0 0 0 0 23 11 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 0 0 0 0 24 40 1 1 0 0 0 25 26 2 0 0 0 0 25 39 1 0 0 0 0 26 38 1 0 0 0 0 27 33 1 0 0 0 0 27 51 1 6 0 0 0 28 35 1 0 0 0 0 28 38 1 1 0 0 0 29 36 1 6 0 0 0 29 52 1 0 0 0 0 30 40 1 6 0 0 0 30 49 1 0 0 0 0 31 43 2 0 0 0 0 31 44 1 0 0 0 0 32 45 2 0 0 0 0 32 51 1 0 0 0 0 33 35 1 0 0 0 0 33 50 1 1 0 0 0 34 46 1 6 0 0 0 34 52 1 0 0 0 0 36 47 1 0 0 0 0 37 7 1 1 0 0 0 37 48 1 0 0 0 0 38 8 1 1 0 0 0 39 40 1 6 0 0 0 40 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	734.42
Volume:	749.914
LogP:	4.317
LogD:	3.156
LogS:	-4.145
# Rotatable Bonds:	12
TPSA:	186.12
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.138
Synthetic Accessibility Score:	5.79
Fsp3:	0.85
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.533
MDCK Permeability:	7.25418358342722e-05
Pgp-inhibitor:	0.355
Pgp-substrate:	0.113
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.648

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	81.0999526977539%
Volume Distribution (VD):	0.479
Pgp-substrate:	7.353067398071289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.437
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	2.085
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.416
Drug-inuced Liver Injury (DILI):	0.581
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.132
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC475243

Natural Product ID:	NPC475243
*Common Name:**	Hebelomic Acid B
IUPAC Name:	(3S)-5-[[(2R,3R,5R,10S,12S,13R,14S,17R)-3,12-diacetyloxy-17-[(2S,3R,6R)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Synonyms:
Standard InCHIKey:	NWNZSOBRAQBTIG-YXLXRQEESA-N
Standard InCHI:	InChI=1S/C40H62O12/c1-21(41)49-30-17-26-25(39(9)16-15-24(40(30,39)10)23-11-14-29(36(5,6)47)52-34(23)46)12-13-28-35(3,4)33(50-22(2)42)27(18-38(26,28)8)51-32(45)20-37(7,48)19-31(43)44/h23-24,27-30,33-34,46-48H,11-20H2,1-10H3,(H,43,44)/t23-,24-,27-,28+,29-,30+,33+,34+,37+,38-,39+,40+/m1/s1
SMILES:	CC(=O)O[C@H]1CC2=C([C@]3([C@@]1(C)[C@H](CC3)[C@H]1CC[C@@H](O[C@@H]1O)C(O)(C)C)C)CC[C@@H]1[C@]2(C)C[C@@H](OC(=O)C[C@](CC(=O)O)(O)C)[C@@H](C1(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501855
PubChem CID:	44584160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO26953	Hebeloma senescens	Species	Cortinariaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[7561908]
NPO26953	Hebeloma senescens	Species	Cortinariaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	386.0	ug ml-1	PMID[541422]

☑ 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 NPC475243 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	250
0.1-0.2	1726
0.2-0.3	5375
0.3-0.4	11465
0.4-0.5	9990
0.5-0.6	6064
0.6-0.7	5274
0.7-0.8	2474
0.8-0.85	56
0.85-0.9	10
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC90630
0.9706	High Similarity	NPC475364
0.9406	High Similarity	NPC218513
0.9406	High Similarity	NPC55954
0.9307	High Similarity	NPC471119
0.9307	High Similarity	NPC296879
0.9143	High Similarity	NPC477069
0.9143	High Similarity	NPC477070
0.9074	High Similarity	NPC116024
0.8972	High Similarity	NPC477073
0.8807	High Similarity	NPC477074
0.8716	High Similarity	NPC233003
0.8704	High Similarity	NPC129340
0.8692	High Similarity	NPC195708
0.8636	High Similarity	NPC251309
0.8624	High Similarity	NPC250481
0.8624	High Similarity	NPC285410
0.8624	High Similarity	NPC263827
0.8611	High Similarity	NPC265655
0.8571	High Similarity	NPC473788
0.8571	High Similarity	NPC475558
0.8455	Intermediate Similarity	NPC292196
0.844	Intermediate Similarity	NPC218853
0.8435	Intermediate Similarity	NPC129434
0.8421	Intermediate Similarity	NPC232258
0.8407	Intermediate Similarity	NPC477252
0.8393	Intermediate Similarity	NPC220293
0.8393	Intermediate Similarity	NPC473882
0.8378	Intermediate Similarity	NPC477253
0.8376	Intermediate Similarity	NPC130229
0.8364	Intermediate Similarity	NPC52241
0.8364	Intermediate Similarity	NPC475317
0.8364	Intermediate Similarity	NPC154856
0.8364	Intermediate Similarity	NPC250956
0.8349	Intermediate Similarity	NPC295389
0.8349	Intermediate Similarity	NPC285576
0.8348	Intermediate Similarity	NPC476849
0.8348	Intermediate Similarity	NPC471406
0.8333	Intermediate Similarity	NPC473199
0.8319	Intermediate Similarity	NPC244127
0.8288	Intermediate Similarity	NPC272242
0.8276	Intermediate Similarity	NPC202051
0.8273	Intermediate Similarity	NPC296761
0.8273	Intermediate Similarity	NPC118225
0.8273	Intermediate Similarity	NPC43976
0.8273	Intermediate Similarity	NPC125361
0.8273	Intermediate Similarity	NPC51925
0.8273	Intermediate Similarity	NPC154085
0.8261	Intermediate Similarity	NPC477071
0.8241	Intermediate Similarity	NPC223741
0.8224	Intermediate Similarity	NPC470053
0.822	Intermediate Similarity	NPC248202
0.8214	Intermediate Similarity	NPC65590
0.8214	Intermediate Similarity	NPC48249
0.8214	Intermediate Similarity	NPC130427
0.8214	Intermediate Similarity	NPC474265
0.8214	Intermediate Similarity	NPC125923
0.8214	Intermediate Similarity	NPC210420
0.8214	Intermediate Similarity	NPC212968
0.8214	Intermediate Similarity	NPC64106
0.8198	Intermediate Similarity	NPC220984
0.8198	Intermediate Similarity	NPC114961
0.8198	Intermediate Similarity	NPC27551
0.8198	Intermediate Similarity	NPC101450
0.8182	Intermediate Similarity	NPC38217
0.8182	Intermediate Similarity	NPC472988
0.8174	Intermediate Similarity	NPC291564
0.8174	Intermediate Similarity	NPC239293
0.8174	Intermediate Similarity	NPC471118
0.8174	Intermediate Similarity	NPC471121
0.8167	Intermediate Similarity	NPC245094
0.8165	Intermediate Similarity	NPC162033
0.8151	Intermediate Similarity	NPC174367
0.8151	Intermediate Similarity	NPC47113
0.8142	Intermediate Similarity	NPC475208
0.8142	Intermediate Similarity	NPC269315
0.8142	Intermediate Similarity	NPC194273
0.8142	Intermediate Similarity	NPC238935
0.8142	Intermediate Similarity	NPC271138
0.8142	Intermediate Similarity	NPC102619
0.8142	Intermediate Similarity	NPC320118
0.8142	Intermediate Similarity	NPC144068
0.8131	Intermediate Similarity	NPC470054
0.8125	Intermediate Similarity	NPC11035
0.8125	Intermediate Similarity	NPC31839
0.8125	Intermediate Similarity	NPC190837
0.8125	Intermediate Similarity	NPC114188
0.8125	Intermediate Similarity	NPC65167
0.8125	Intermediate Similarity	NPC472003
0.812	Intermediate Similarity	NPC187950
0.812	Intermediate Similarity	NPC278163
0.812	Intermediate Similarity	NPC475182
0.8108	Intermediate Similarity	NPC91583
0.8108	Intermediate Similarity	NPC240125
0.8108	Intermediate Similarity	NPC137917
0.8103	Intermediate Similarity	NPC25663
0.8103	Intermediate Similarity	NPC51564
0.8103	Intermediate Similarity	NPC135849
0.8099	Intermediate Similarity	NPC476966
0.8091	Intermediate Similarity	NPC234160
0.8091	Intermediate Similarity	NPC293512
0.8087	Intermediate Similarity	NPC471120
0.8087	Intermediate Similarity	NPC471117
0.8087	Intermediate Similarity	NPC470171
0.8073	Intermediate Similarity	NPC470885
0.8073	Intermediate Similarity	NPC85593
0.8073	Intermediate Similarity	NPC221562
0.8073	Intermediate Similarity	NPC31430
0.8073	Intermediate Similarity	NPC187400
0.807	Intermediate Similarity	NPC475633
0.807	Intermediate Similarity	NPC474557
0.807	Intermediate Similarity	NPC243354
0.8056	Intermediate Similarity	NPC136816
0.8056	Intermediate Similarity	NPC154452
0.8053	Intermediate Similarity	NPC161434
0.8053	Intermediate Similarity	NPC80843
0.8053	Intermediate Similarity	NPC195132
0.8053	Intermediate Similarity	NPC46388
0.8053	Intermediate Similarity	NPC1046
0.8053	Intermediate Similarity	NPC116794
0.8053	Intermediate Similarity	NPC470543
0.8053	Intermediate Similarity	NPC37739
0.8053	Intermediate Similarity	NPC243572
0.8051	Intermediate Similarity	NPC156789
0.8036	Intermediate Similarity	NPC199457
0.8036	Intermediate Similarity	NPC269095
0.8036	Intermediate Similarity	NPC108709
0.8036	Intermediate Similarity	NPC75747
0.8036	Intermediate Similarity	NPC102914
0.8036	Intermediate Similarity	NPC7870
0.8036	Intermediate Similarity	NPC242611
0.8036	Intermediate Similarity	NPC110139
0.8036	Intermediate Similarity	NPC78046
0.8036	Intermediate Similarity	NPC68419
0.8036	Intermediate Similarity	NPC274507
0.8034	Intermediate Similarity	NPC472076
0.8034	Intermediate Similarity	NPC142151
0.8034	Intermediate Similarity	NPC110385
0.8034	Intermediate Similarity	NPC267694
0.8034	Intermediate Similarity	NPC473645
0.8034	Intermediate Similarity	NPC472075
0.8034	Intermediate Similarity	NPC144644
0.8034	Intermediate Similarity	NPC476991
0.8034	Intermediate Similarity	NPC37860
0.8034	Intermediate Similarity	NPC153673
0.8033	Intermediate Similarity	NPC173347
0.8018	Intermediate Similarity	NPC258323
0.8018	Intermediate Similarity	NPC88744
0.8018	Intermediate Similarity	NPC295980
0.8018	Intermediate Similarity	NPC224414
0.8017	Intermediate Similarity	NPC276758
0.8017	Intermediate Similarity	NPC297179
0.8017	Intermediate Similarity	NPC86020
0.8017	Intermediate Similarity	NPC311534
0.8017	Intermediate Similarity	NPC475632
0.8017	Intermediate Similarity	NPC18233
0.8	Intermediate Similarity	NPC104427
0.8	Intermediate Similarity	NPC146652
0.8	Intermediate Similarity	NPC279638
0.8	Intermediate Similarity	NPC88945
0.8	Intermediate Similarity	NPC470767
0.8	Intermediate Similarity	NPC475494
0.8	Intermediate Similarity	NPC470763
0.8	Intermediate Similarity	NPC210178
0.7983	Intermediate Similarity	NPC160084
0.7983	Intermediate Similarity	NPC478066
0.7982	Intermediate Similarity	NPC47063
0.7982	Intermediate Similarity	NPC204458
0.7982	Intermediate Similarity	NPC260665
0.7982	Intermediate Similarity	NPC200944
0.7982	Intermediate Similarity	NPC189884
0.7982	Intermediate Similarity	NPC146563
0.7982	Intermediate Similarity	NPC255017
0.7982	Intermediate Similarity	NPC132668
0.7982	Intermediate Similarity	NPC138334
0.7982	Intermediate Similarity	NPC73986
0.7982	Intermediate Similarity	NPC73455
0.7981	Intermediate Similarity	NPC27918
0.7966	Intermediate Similarity	NPC275225
0.7966	Intermediate Similarity	NPC75417
0.7966	Intermediate Similarity	NPC293031
0.7966	Intermediate Similarity	NPC68767
0.7966	Intermediate Similarity	NPC51099
0.7965	Intermediate Similarity	NPC108748
0.7965	Intermediate Similarity	NPC297208
0.7965	Intermediate Similarity	NPC30397
0.7965	Intermediate Similarity	NPC471243
0.7965	Intermediate Similarity	NPC179434
0.7965	Intermediate Similarity	NPC191763
0.7965	Intermediate Similarity	NPC269466
0.7965	Intermediate Similarity	NPC235841
0.7965	Intermediate Similarity	NPC211798
0.7965	Intermediate Similarity	NPC473481
0.7963	Intermediate Similarity	NPC121072
0.7963	Intermediate Similarity	NPC88000
0.7963	Intermediate Similarity	NPC47566
0.7963	Intermediate Similarity	NPC309425
0.7963	Intermediate Similarity	NPC472023
0.7963	Intermediate Similarity	NPC21064
0.7963	Intermediate Similarity	NPC129372

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 NPC475243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	2122
0.2-0.3	4004
0.3-0.4	1824
0.4-0.5	497
0.5-0.6	259
0.6-0.7	179
0.7-0.8	40
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
0.8273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8087	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7319	Approved
0.7581	Intermediate Similarity	NPD7736	Approved
0.7561	Intermediate Similarity	NPD7507	Approved
0.7541	Intermediate Similarity	NPD8328	Phase 3
0.7521	Intermediate Similarity	NPD8033	Approved
0.7521	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7456	Intermediate Similarity	NPD6412	Phase 2
0.7438	Intermediate Similarity	NPD8377	Approved
0.7438	Intermediate Similarity	NPD8294	Approved
0.7417	Intermediate Similarity	NPD7328	Approved
0.7417	Intermediate Similarity	NPD7327	Approved
0.7377	Intermediate Similarity	NPD8378	Approved
0.7377	Intermediate Similarity	NPD8380	Approved
0.7377	Intermediate Similarity	NPD8335	Approved
0.7377	Intermediate Similarity	NPD8379	Approved
0.7377	Intermediate Similarity	NPD8296	Approved
0.7317	Intermediate Similarity	NPD6370	Approved
0.7295	Intermediate Similarity	NPD6319	Approved
0.7236	Intermediate Similarity	NPD8515	Approved
0.7236	Intermediate Similarity	NPD7503	Approved
0.7236	Intermediate Similarity	NPD8517	Approved
0.7236	Intermediate Similarity	NPD8516	Approved
0.7236	Intermediate Similarity	NPD8513	Phase 3
0.72	Intermediate Similarity	NPD7492	Approved
0.719	Intermediate Similarity	NPD7115	Discovery
0.7154	Intermediate Similarity	NPD6059	Approved
0.7154	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.7094	Intermediate Similarity	NPD6686	Approved
0.7087	Intermediate Similarity	NPD7078	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6882	Approved
0.6991	Remote Similarity	NPD7638	Approved
0.6983	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6015	Approved
0.696	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD7639	Approved
0.693	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6911	Remote Similarity	NPD6009	Approved
0.6909	Remote Similarity	NPD6411	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6891	Remote Similarity	NPD6373	Approved
0.6891	Remote Similarity	NPD6372	Approved
0.6847	Remote Similarity	NPD6399	Phase 3
0.6833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7632	Discontinued
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6807	Remote Similarity	NPD7320	Approved
0.6777	Remote Similarity	NPD8130	Phase 1
0.6777	Remote Similarity	NPD6650	Approved
0.6777	Remote Similarity	NPD6649	Approved
0.6757	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6101	Approved
0.6723	Remote Similarity	NPD5701	Approved
0.6723	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD8171	Discontinued
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6033	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6008	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6637	Remote Similarity	NPD7748	Approved
0.6612	Remote Similarity	NPD6014	Approved
0.6612	Remote Similarity	NPD6013	Approved
0.6612	Remote Similarity	NPD6012	Approved
0.6609	Remote Similarity	NPD6083	Phase 2
0.6609	Remote Similarity	NPD6084	Phase 2
0.6607	Remote Similarity	NPD7637	Suspended
0.6589	Remote Similarity	NPD7604	Phase 2
0.6583	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5695	Phase 3
0.6577	Remote Similarity	NPD5328	Approved
0.6574	Remote Similarity	NPD4786	Approved
0.6565	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD5983	Phase 2
0.6549	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD5778	Approved
0.6545	Remote Similarity	NPD7524	Approved
0.6529	Remote Similarity	NPD6011	Approved
0.6508	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6336	Discontinued
0.6476	Remote Similarity	NPD6697	Approved
0.6476	Remote Similarity	NPD6115	Approved
0.6476	Remote Similarity	NPD6114	Approved
0.6476	Remote Similarity	NPD6118	Approved
0.6466	Remote Similarity	NPD7902	Approved
0.6466	Remote Similarity	NPD4755	Approved
0.6462	Remote Similarity	NPD6067	Discontinued
0.646	Remote Similarity	NPD7515	Phase 2
0.646	Remote Similarity	NPD6079	Approved
0.6444	Remote Similarity	NPD8338	Approved
0.6434	Remote Similarity	NPD6921	Approved
0.641	Remote Similarity	NPD5696	Approved
0.6391	Remote Similarity	NPD8337	Approved
0.6391	Remote Similarity	NPD8336	Approved
0.6389	Remote Similarity	NPD3667	Approved
0.6371	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5285	Approved
0.6356	Remote Similarity	NPD5286	Approved
0.6356	Remote Similarity	NPD4700	Approved
0.6356	Remote Similarity	NPD4696	Approved
0.6355	Remote Similarity	NPD4748	Discontinued
0.6355	Remote Similarity	NPD7525	Registered
0.633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3669	Approved
0.632	Remote Similarity	NPD6053	Discontinued
0.6316	Remote Similarity	NPD7983	Approved
0.6308	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3618	Phase 1
0.6299	Remote Similarity	NPD6274	Approved
0.6299	Remote Similarity	NPD6940	Discontinued
0.6286	Remote Similarity	NPD6117	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6261	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD8080	Discontinued
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD5222	Approved
0.6239	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4697	Phase 3
0.6239	Remote Similarity	NPD5221	Approved
0.623	Remote Similarity	NPD4767	Approved
0.623	Remote Similarity	NPD4768	Approved
0.6226	Remote Similarity	NPD6116	Phase 1
0.6207	Remote Similarity	NPD7900	Approved
0.6207	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8449	Approved
0.6202	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD5174	Approved
0.6198	Remote Similarity	NPD5175	Approved
0.6195	Remote Similarity	NPD6672	Approved
0.6195	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5737	Approved
0.619	Remote Similarity	NPD7339	Approved
0.619	Remote Similarity	NPD6942	Approved
0.6186	Remote Similarity	NPD5173	Approved
0.6183	Remote Similarity	NPD6908	Approved
0.6183	Remote Similarity	NPD6909	Approved
0.6182	Remote Similarity	NPD6695	Phase 3
0.6172	Remote Similarity	NPD6868	Approved
0.6167	Remote Similarity	NPD5223	Approved
0.6167	Remote Similarity	NPD1700	Approved
0.6167	Remote Similarity	NPD4159	Approved
0.6167	Remote Similarity	NPD5344	Discontinued
0.6161	Remote Similarity	NPD6684	Approved
0.6161	Remote Similarity	NPD7334	Approved
0.6161	Remote Similarity	NPD5330	Approved
0.6161	Remote Similarity	NPD7521	Approved
0.6161	Remote Similarity	NPD6409	Approved
0.6161	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7146	Approved
0.6159	Remote Similarity	NPD8450	Suspended
0.6154	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD4753	Phase 2
0.6131	Remote Similarity	NPD7260	Phase 2
0.6129	Remote Similarity	NPD4729	Approved
0.6129	Remote Similarity	NPD4730	Approved
0.6126	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6317	Approved
0.6111	Remote Similarity	NPD7645	Phase 2
0.6106	Remote Similarity	NPD3573	Approved
0.6106	Remote Similarity	NPD7750	Discontinued
0.6102	Remote Similarity	NPD7839	Suspended
0.6096	Remote Similarity	NPD7625	Phase 1
0.6095	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD46	Approved
0.6087	Remote Similarity	NPD6698	Approved
0.6077	Remote Similarity	NPD6313	Approved
0.6077	Remote Similarity	NPD6314	Approved
0.6066	Remote Similarity	NPD4754	Approved
0.6058	Remote Similarity	NPD5956	Approved
0.6055	Remote Similarity	NPD6928	Phase 2
0.6053	Remote Similarity	NPD6903	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