NPASS Compound

Structure

CID126002 OpenBabel06191715482D 37 41 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5622 1.3660 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 -0.8660 -0.5000 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 3.4641 -3.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 5.1962 -1.0000 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 1.7321 -0.0000 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 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1 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 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 1 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 2 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 33 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 27 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 32 1 0 0 0 0 15 35 1 0 0 0 0 16 34 1 0 0 0 0 17 23 1 0 0 0 0 17 28 1 0 0 0 0 18 24 1 0 0 0 0 18 25 2 0 0 0 0 19 31 1 0 0 0 0 20 29 2 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 0 0 0 0 23 33 1 1 0 0 0 24 30 2 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 19 1 6 0 0 0 26 27 1 0 0 0 0 27 34 1 1 0 0 0 28 34 1 1 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 31 32 1 0 0 0 0 31 35 1 6 0 0 0 33 37 1 0 0 0 0 34 8 1 1 0 0 0 35 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.41
Volume:	578.168
LogP:	8.604
LogD:	5.933
LogS:	-5.897
# Rotatable Bonds:	3
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.401
Synthetic Accessibility Score:	4.824
Fsp3:	0.771
Lipinski Rule-of-5:	Rejected
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:	-5.367
MDCK Permeability:	9.209393283526879e-06
Pgp-inhibitor:	0.982
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.093
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	98.09992218017578%
Volume Distribution (VD):	1.919
Pgp-substrate:	2.490546226501465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.373
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.63
CYP2D6-inhibitor:	0.469
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.628
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	6.047
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.798
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.529
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.628
Carcinogencity:	0.11
Eye Corrosion:	0.01
Eye Irritation:	0.737
Respiratory Toxicity:	0.751

Download Data

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

Natural Product: NPC126002

Natural Product ID:	NPC126002
*Common Name:**	Ferrugieudesmol
IUPAC Name:	(4bS,8aS,10R)-10-[(1S,4aS,6R,8aS)-6-(2-hydroxypropan-2-yl)-8a-methyl-4-methylidene-1,2,3,4a,5,6,7,8-octahydronaphthalen-1-yl]-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-3-ol
Synonyms:	Ferrugieudesmol
Standard InCHIKey:	QJDFWYBXQNDEJQ-RPABJFINSA-N
Standard InCHI:	InChI=1S/C35H54O2/c1-21(2)24-18-25-26(19-31-32(4,5)14-10-15-35(31,9)29(25)20-30(24)36)27-12-11-22(3)28-17-23(33(6,7)37)13-16-34(27,28)8/h18,20-21,23,26-28,31,36-37H,3,10-17,19H2,1-2,4-9H3/t23-,26+,27+,28+,31+,34+,35-/m1/s1
SMILES:	C=C1CC[C@H]([C@]2([C@H]1C[C@@H](CC2)C(O)(C)C)C)[C@H]1C[C@H]2C(C)(C)CCC[C@@]2(c2c1cc(C(C)C)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508557
PubChem CID:	11994700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO14832.1	Calocedrus macrolepis var. formosana	Varieties	Cupressaceae	Eukaryota	bark	n.a.	n.a.	PMID[17125231]
NPO17318	Streptomyces cyaneus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21462031]
NPO14832.1	Calocedrus macrolepis var. formosana	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14832.1	Calocedrus macrolepis var. formosana	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12311	Graphis handelii	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14653	Haliotis diversicolor	Species	Haliotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14339	Fevillea trilobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25141	Mycetinis alliaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17251	Aniba firmula	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3705	Anacardium humile	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13361	Clerodendrum tomentosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17158	Trichocereus bridgesii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17318	Streptomyces cyaneus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5124	Aconitum ibukiense	Species	Ranunculaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	11400.0	nM	PMID[494321]

☑ 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 NPC126002 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	395
0.1-0.2	1820
0.2-0.3	4055
0.3-0.4	8547
0.4-0.5	10760
0.5-0.6	12016
0.6-0.7	4175
0.7-0.8	802
0.8-0.85	95
0.85-0.9	27
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9821	High Similarity	NPC93071
0.9554	High Similarity	NPC471668
0.9279	High Similarity	NPC260323
0.9279	High Similarity	NPC176279
0.9123	High Similarity	NPC192948
0.9123	High Similarity	NPC35797
0.9043	High Similarity	NPC38893
0.9043	High Similarity	NPC308311
0.9043	High Similarity	NPC477137
0.9035	High Similarity	NPC195922
0.9027	High Similarity	NPC250323
0.9018	High Similarity	NPC141782
0.8966	High Similarity	NPC304510
0.8966	High Similarity	NPC172219
0.8919	High Similarity	NPC151477
0.8889	High Similarity	NPC471671
0.8879	High Similarity	NPC219112
0.887	High Similarity	NPC268160
0.886	High Similarity	NPC46940
0.885	High Similarity	NPC13482
0.8833	High Similarity	NPC71094
0.8814	High Similarity	NPC469644
0.8803	High Similarity	NPC477136
0.8793	High Similarity	NPC147179
0.8793	High Similarity	NPC469719
0.8783	High Similarity	NPC715
0.8772	High Similarity	NPC95716
0.8739	High Similarity	NPC117115
0.8729	High Similarity	NPC206
0.8718	High Similarity	NPC141001
0.8718	High Similarity	NPC92
0.8718	High Similarity	NPC469663
0.8718	High Similarity	NPC308828
0.8673	High Similarity	NPC11554
0.8661	High Similarity	NPC21594
0.8644	High Similarity	NPC16030
0.8644	High Similarity	NPC299180
0.8621	High Similarity	NPC322239
0.8621	High Similarity	NPC321589
0.8609	High Similarity	NPC322753
0.8609	High Similarity	NPC151537
0.8609	High Similarity	NPC77772
0.8596	High Similarity	NPC58865
0.8595	High Similarity	NPC249340
0.8595	High Similarity	NPC162935
0.8583	High Similarity	NPC260832
0.8583	High Similarity	NPC135467
0.8571	High Similarity	NPC469609
0.8571	High Similarity	NPC154030
0.8547	High Similarity	NPC471534
0.8534	High Similarity	NPC62867
0.8534	High Similarity	NPC177962
0.8534	High Similarity	NPC228425
0.8525	High Similarity	NPC11250
0.8522	High Similarity	NPC132720
0.8512	High Similarity	NPC32322
0.8512	High Similarity	NPC259703
0.85	High Similarity	NPC151197
0.848	Intermediate Similarity	NPC108164
0.8462	Intermediate Similarity	NPC317869
0.8455	Intermediate Similarity	NPC471187
0.8448	Intermediate Similarity	NPC266937
0.8448	Intermediate Similarity	NPC470770
0.8448	Intermediate Similarity	NPC469912
0.8443	Intermediate Similarity	NPC154696
0.8435	Intermediate Similarity	NPC314187
0.84	Intermediate Similarity	NPC321822
0.84	Intermediate Similarity	NPC43000
0.84	Intermediate Similarity	NPC325294
0.84	Intermediate Similarity	NPC100414
0.8387	Intermediate Similarity	NPC181334
0.8378	Intermediate Similarity	NPC211885
0.8376	Intermediate Similarity	NPC471179
0.8374	Intermediate Similarity	NPC176208
0.8374	Intermediate Similarity	NPC297057
0.8374	Intermediate Similarity	NPC478058
0.8362	Intermediate Similarity	NPC296683
0.8361	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC471077
0.8333	Intermediate Similarity	NPC271274
0.832	Intermediate Similarity	NPC124030
0.832	Intermediate Similarity	NPC137750
0.8305	Intermediate Similarity	NPC263753
0.8304	Intermediate Similarity	NPC252105
0.8293	Intermediate Similarity	NPC253627
0.8279	Intermediate Similarity	NPC99734
0.8268	Intermediate Similarity	NPC47288
0.8264	Intermediate Similarity	NPC164649
0.8264	Intermediate Similarity	NPC48342
0.8261	Intermediate Similarity	NPC320439
0.825	Intermediate Similarity	NPC474387
0.825	Intermediate Similarity	NPC247858
0.825	Intermediate Similarity	NPC154511
0.825	Intermediate Similarity	NPC261973
0.825	Intermediate Similarity	NPC474358
0.825	Intermediate Similarity	NPC257540
0.825	Intermediate Similarity	NPC137496
0.8246	Intermediate Similarity	NPC219286
0.8246	Intermediate Similarity	NPC99557
0.8226	Intermediate Similarity	NPC121168
0.8226	Intermediate Similarity	NPC471794
0.8217	Intermediate Similarity	NPC243305
0.8214	Intermediate Similarity	NPC72729
0.8214	Intermediate Similarity	NPC225506
0.8211	Intermediate Similarity	NPC328504
0.8203	Intermediate Similarity	NPC86257
0.8197	Intermediate Similarity	NPC42657
0.8189	Intermediate Similarity	NPC176130
0.8189	Intermediate Similarity	NPC69424
0.8189	Intermediate Similarity	NPC84672
0.8189	Intermediate Similarity	NPC78364
0.8174	Intermediate Similarity	NPC53740
0.8167	Intermediate Similarity	NPC84999
0.8167	Intermediate Similarity	NPC246760
0.816	Intermediate Similarity	NPC198014
0.8158	Intermediate Similarity	NPC272029
0.8158	Intermediate Similarity	NPC238696
0.8154	Intermediate Similarity	NPC85595
0.8154	Intermediate Similarity	NPC289624
0.8154	Intermediate Similarity	NPC321086
0.8154	Intermediate Similarity	NPC27578
0.814	Intermediate Similarity	NPC472793
0.814	Intermediate Similarity	NPC108129
0.813	Intermediate Similarity	NPC318552
0.813	Intermediate Similarity	NPC478121
0.813	Intermediate Similarity	NPC190501
0.8125	Intermediate Similarity	NPC201069
0.8125	Intermediate Similarity	NPC33675
0.8125	Intermediate Similarity	NPC252821
0.8125	Intermediate Similarity	NPC299762
0.8125	Intermediate Similarity	NPC122005
0.811	Intermediate Similarity	NPC9292
0.811	Intermediate Similarity	NPC145659
0.8106	Intermediate Similarity	NPC103082
0.8103	Intermediate Similarity	NPC27252
0.8103	Intermediate Similarity	NPC472979
0.8092	Intermediate Similarity	NPC476282
0.8087	Intermediate Similarity	NPC47284
0.8087	Intermediate Similarity	NPC138942
0.8083	Intermediate Similarity	NPC249270
0.8083	Intermediate Similarity	NPC107240
0.808	Intermediate Similarity	NPC152946
0.8077	Intermediate Similarity	NPC473047
0.8077	Intermediate Similarity	NPC153019
0.807	Intermediate Similarity	NPC269212
0.807	Intermediate Similarity	NPC168829
0.8062	Intermediate Similarity	NPC303910
0.8062	Intermediate Similarity	NPC276238
0.8051	Intermediate Similarity	NPC224870
0.8049	Intermediate Similarity	NPC176893
0.8049	Intermediate Similarity	NPC323074
0.8047	Intermediate Similarity	NPC476536
0.8047	Intermediate Similarity	NPC72667
0.8047	Intermediate Similarity	NPC186889
0.8036	Intermediate Similarity	NPC79241
0.8036	Intermediate Similarity	NPC77492
0.8036	Intermediate Similarity	NPC6597
0.8031	Intermediate Similarity	NPC4286
0.8031	Intermediate Similarity	NPC76119
0.8031	Intermediate Similarity	NPC87985
0.8018	Intermediate Similarity	NPC222146
0.8018	Intermediate Similarity	NPC144682
0.8017	Intermediate Similarity	NPC474486
0.8017	Intermediate Similarity	NPC155072
0.8017	Intermediate Similarity	NPC469913
0.8017	Intermediate Similarity	NPC310456
0.8016	Intermediate Similarity	NPC12824
0.8	Intermediate Similarity	NPC77569
0.8	Intermediate Similarity	NPC117846
0.8	Intermediate Similarity	NPC142198
0.8	Intermediate Similarity	NPC472369
0.8	Intermediate Similarity	NPC23804
0.8	Intermediate Similarity	NPC474115
0.8	Intermediate Similarity	NPC288411
0.7985	Intermediate Similarity	NPC49911
0.7984	Intermediate Similarity	NPC68339
0.7984	Intermediate Similarity	NPC477037
0.7984	Intermediate Similarity	NPC475245
0.7984	Intermediate Similarity	NPC69006
0.7984	Intermediate Similarity	NPC103916
0.7984	Intermediate Similarity	NPC325544
0.7984	Intermediate Similarity	NPC318581
0.7982	Intermediate Similarity	NPC51015
0.7982	Intermediate Similarity	NPC477685
0.7969	Intermediate Similarity	NPC254492
0.7965	Intermediate Similarity	NPC92730
0.7955	Intermediate Similarity	NPC211352
0.7955	Intermediate Similarity	NPC473665
0.7955	Intermediate Similarity	NPC475627
0.7955	Intermediate Similarity	NPC18982
0.7955	Intermediate Similarity	NPC475346
0.7955	Intermediate Similarity	NPC475457
0.7955	Intermediate Similarity	NPC49742
0.7953	Intermediate Similarity	NPC265413
0.7953	Intermediate Similarity	NPC10154
0.7953	Intermediate Similarity	NPC248557
0.7953	Intermediate Similarity	NPC224342
0.7953	Intermediate Similarity	NPC199273
0.7951	Intermediate Similarity	NPC312105
0.7951	Intermediate Similarity	NPC115808

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 NPC126002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	972
0.2-0.3	1358
0.3-0.4	3041
0.4-0.5	2046
0.5-0.6	1071
0.6-0.7	234
0.7-0.8	61
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8376	Intermediate Similarity	NPD7635	Approved
0.8279	Intermediate Similarity	NPD4059	Approved
0.8264	Intermediate Similarity	NPD3091	Approved
0.8261	Intermediate Similarity	NPD2342	Discontinued
0.813	Intermediate Similarity	NPD3019	Approved
0.8018	Intermediate Similarity	NPD1809	Phase 2
0.8	Intermediate Similarity	NPD3092	Approved
0.7984	Intermediate Similarity	NPD2932	Approved
0.7965	Intermediate Similarity	NPD3020	Approved
0.7946	Intermediate Similarity	NPD288	Approved
0.7857	Intermediate Similarity	NPD844	Approved
0.784	Intermediate Similarity	NPD3095	Discontinued
0.7815	Intermediate Similarity	NPD4750	Phase 3
0.7769	Intermediate Similarity	NPD5736	Approved
0.7768	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3094	Phase 2
0.7739	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD2859	Approved
0.7699	Intermediate Similarity	NPD2860	Approved
0.7698	Intermediate Similarity	NPD2286	Discontinued
0.7679	Intermediate Similarity	NPD845	Approved
0.7667	Intermediate Similarity	NPD3022	Approved
0.7667	Intermediate Similarity	NPD3021	Approved
0.763	Intermediate Similarity	NPD4097	Suspended
0.7619	Intermediate Similarity	NPD4093	Discontinued
0.7611	Intermediate Similarity	NPD2934	Approved
0.7611	Intermediate Similarity	NPD2933	Approved
0.7597	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2605	Approved
0.7576	Intermediate Similarity	NPD2606	Approved
0.7559	Intermediate Similarity	NPD1751	Approved
0.7557	Intermediate Similarity	NPD4624	Approved
0.7541	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6696	Suspended
0.7537	Intermediate Similarity	NPD6663	Approved
0.752	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5155	Approved
0.7519	Intermediate Similarity	NPD5156	Approved
0.75	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD3023	Approved
0.75	Intermediate Similarity	NPD3026	Approved
0.75	Intermediate Similarity	NPD8166	Discontinued
0.748	Intermediate Similarity	NPD3024	Approved
0.748	Intermediate Similarity	NPD3025	Approved
0.7444	Intermediate Similarity	NPD3595	Approved
0.7444	Intermediate Similarity	NPD3594	Approved
0.7422	Intermediate Similarity	NPD4626	Approved
0.7419	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7742	Approved
0.7391	Intermediate Similarity	NPD7743	Approved
0.7388	Intermediate Similarity	NPD4625	Phase 3
0.7381	Intermediate Similarity	NPD7340	Approved
0.7368	Intermediate Similarity	NPD3636	Approved
0.7368	Intermediate Similarity	NPD3635	Approved
0.7368	Intermediate Similarity	NPD3637	Approved
0.7353	Intermediate Similarity	NPD3620	Phase 2
0.7353	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5327	Phase 3
0.7293	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2194	Approved
0.7293	Intermediate Similarity	NPD2195	Approved
0.7287	Intermediate Similarity	NPD4589	Approved
0.7286	Intermediate Similarity	NPD4726	Approved
0.7286	Intermediate Similarity	NPD4721	Approved
0.7286	Intermediate Similarity	NPD4725	Approved
0.728	Intermediate Similarity	NPD2229	Approved
0.728	Intermediate Similarity	NPD2234	Approved
0.728	Intermediate Similarity	NPD2228	Approved
0.7246	Intermediate Similarity	NPD6353	Approved
0.7236	Intermediate Similarity	NPD1792	Phase 2
0.7227	Intermediate Similarity	NPD846	Approved
0.7227	Intermediate Similarity	NPD940	Approved
0.7222	Intermediate Similarity	NPD497	Approved
0.7218	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5408	Approved
0.7214	Intermediate Similarity	NPD5404	Approved
0.7214	Intermediate Similarity	NPD5405	Approved
0.7214	Intermediate Similarity	NPD5406	Approved
0.7203	Intermediate Similarity	NPD8131	Suspended
0.7197	Intermediate Similarity	NPD4749	Approved
0.7194	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1201	Approved
0.7174	Intermediate Similarity	NPD5735	Approved
0.7165	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD495	Approved
0.7143	Intermediate Similarity	NPD498	Approved
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7143	Intermediate Similarity	NPD496	Approved
0.7132	Intermediate Similarity	NPD5303	Approved
0.7132	Intermediate Similarity	NPD7330	Discontinued
0.7132	Intermediate Similarity	NPD5304	Approved
0.7101	Intermediate Similarity	NPD4140	Approved
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7092	Intermediate Similarity	NPD6100	Approved
0.7092	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5691	Approved
0.7055	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8032	Phase 2
0.7025	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1283	Approved
0.7	Intermediate Similarity	NPD1242	Phase 1
0.7	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1444	Approved
0.6992	Remote Similarity	NPD1445	Approved
0.6986	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7041	Phase 2
0.698	Remote Similarity	NPD7458	Discontinued
0.6964	Remote Similarity	NPD111	Approved
0.6963	Remote Similarity	NPD1470	Approved
0.6947	Remote Similarity	NPD1651	Approved
0.6947	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3638	Discontinued
0.6934	Remote Similarity	NPD4908	Phase 1
0.6884	Remote Similarity	NPD7095	Approved
0.6875	Remote Similarity	NPD7037	Approved
0.6871	Remote Similarity	NPD2420	Approved
0.6871	Remote Similarity	NPD2421	Approved
0.687	Remote Similarity	NPD7741	Discontinued
0.6866	Remote Similarity	NPD2232	Approved
0.6866	Remote Similarity	NPD2230	Approved
0.6866	Remote Similarity	NPD2233	Approved
0.6861	Remote Similarity	NPD2861	Phase 2
0.6846	Remote Similarity	NPD7636	Approved
0.6842	Remote Similarity	NPD3143	Discontinued
0.6835	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6674	Discontinued
0.6822	Remote Similarity	NPD5951	Approved
0.6791	Remote Similarity	NPD1281	Approved
0.6781	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7725	Approved
0.6765	Remote Similarity	NPD8651	Approved
0.6759	Remote Similarity	NPD4257	Approved
0.6759	Remote Similarity	NPD4256	Phase 2
0.6753	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD9500	Approved
0.6744	Remote Similarity	NPD5283	Phase 1
0.6741	Remote Similarity	NPD3070	Discontinued
0.6738	Remote Similarity	NPD3109	Approved
0.6738	Remote Similarity	NPD3110	Approved
0.6721	Remote Similarity	NPD3028	Approved
0.6716	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7294	Phase 1
0.6712	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3645	Discontinued
0.6692	Remote Similarity	NPD1793	Approved
0.6692	Remote Similarity	NPD1791	Approved
0.6691	Remote Similarity	NPD1669	Approved
0.669	Remote Similarity	NPD3657	Discovery
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD7831	Phase 2
0.6667	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD7833	Phase 2
0.6667	Remote Similarity	NPD7644	Approved
0.6643	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2668	Approved
0.6642	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2667	Approved
0.6642	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD709	Approved
0.6641	Remote Similarity	NPD7157	Approved
0.662	Remote Similarity	NPD6346	Approved
0.6619	Remote Similarity	NPD4208	Discontinued
0.6599	Remote Similarity	NPD2209	Approved
0.6599	Remote Similarity	NPD2211	Approved
0.6597	Remote Similarity	NPD7097	Phase 1
0.6596	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD228	Approved
0.6577	Remote Similarity	NPD3300	Phase 2
0.6565	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5451	Approved
0.6562	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6090	Discontinued
0.6541	Remote Similarity	NPD7610	Discontinued
0.6528	Remote Similarity	NPD2157	Approved
0.6515	Remote Similarity	NPD4198	Discontinued
0.6515	Remote Similarity	NPD6387	Discontinued
0.6503	Remote Similarity	NPD2238	Phase 2
0.6503	Remote Similarity	NPD2979	Phase 3
0.65	Remote Similarity	NPD4212	Discontinued
0.649	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3764	Approved
0.6475	Remote Similarity	NPD1164	Approved
0.6475	Remote Similarity	NPD4103	Phase 2
0.6475	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5929	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