NPASS Compound

Structure

CID82538 OpenBabel06191715422D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.6275 -0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1483 0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3496 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 -1.1049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 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 -1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8368 -1.1049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 28 1 0 0 0 0 7 8 2 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 16 29 1 0 0 0 0 17 27 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 23 27 1 1 0 0 0 23 33 1 0 0 0 0 24 30 1 1 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 6 0 0 0 29 6 1 6 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.006
LogD:	3.456
LogS:	-4.067
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	5.144
Fsp3:	0.867
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:	-5.218
MDCK Permeability:	1.4765709238417912e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.338
Plasma Protein Binding (PPB):	89.87773895263672%
Volume Distribution (VD):	0.816
Pgp-substrate:	6.255874156951904%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.809

ADMET: Excretion

Clearance (CL):	7.044
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.463
Human Hepatotoxicity (H-HT):	0.569
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.714
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.258
Carcinogencity:	0.126
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC82538

Natural Product ID:	NPC82538
*Common Name:**	Saikogenin A
IUPAC Name:	(3S,4R,4aR,6aR,6bS,8S,8aS,14aR,14bS)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicene-3,8-diol
Synonyms:
Standard InCHIKey:	QGNVMEXLLPGQEV-HSFRRAFJSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)13-14-30(18-32)20(15-25)19-7-8-22-26(3)11-10-23(33)27(4,17-31)21(26)9-12-28(22,5)29(19,6)16-24(30)34/h7-8,21-24,31-34H,9-18H2,1-6H3/t21-,22-,23+,24+,26+,27+,28-,29-,30-/m1/s1
SMILES:	OC[C@@]12CCC(CC2=C2[C@](C[C@@H]1O)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1C=C2)(C)CC[C@@H]([C@@]3(C)CO)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3792476
PubChem CID:	99651
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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	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	5
Others	3

Activity Type	# Activity
Cell Line	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	80000.0	nM	PMID[552622]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	80000.0	nM	PMID[552622]
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	>	80000.0	nM	PMID[552622]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	80000.0	nM	PMID[552622]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	81.36	%	PMID[552622]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	79.87	%	PMID[552622]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	78.01	%	PMID[552622]
NPT27	Others	Unspecified		IC50	>	80000.0	nM	PMID[552622]

☑ 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 NPC82538 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	198
0.1-0.2	1348
0.2-0.3	5139
0.3-0.4	15439
0.4-0.5	9781
0.5-0.6	5698
0.6-0.7	3767
0.7-0.8	1143
0.8-0.85	130
0.85-0.9	48
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC237795
0.9351	High Similarity	NPC72507
0.9231	High Similarity	NPC53744
0.9103	High Similarity	NPC99168
0.9103	High Similarity	NPC474989
0.9103	High Similarity	NPC253807
0.9103	High Similarity	NPC22955
0.9103	High Similarity	NPC196753
0.9103	High Similarity	NPC98386
0.9103	High Similarity	NPC230295
0.9103	High Similarity	NPC470396
0.9103	High Similarity	NPC158662
0.8987	High Similarity	NPC291379
0.8974	High Similarity	NPC101475
0.8974	High Similarity	NPC40394
0.8974	High Similarity	NPC34177
0.8974	High Similarity	NPC157996
0.8902	High Similarity	NPC238992
0.8889	High Similarity	NPC47763
0.8861	High Similarity	NPC300499
0.8851	High Similarity	NPC80365
0.8846	High Similarity	NPC30590
0.8846	High Similarity	NPC122418
0.8846	High Similarity	NPC106432
0.8846	High Similarity	NPC106364
0.8846	High Similarity	NPC27765
0.8846	High Similarity	NPC265328
0.8846	High Similarity	NPC290598
0.8846	High Similarity	NPC120098
0.8831	High Similarity	NPC100334
0.8831	High Similarity	NPC243342
0.8831	High Similarity	NPC91858
0.8831	High Similarity	NPC471797
0.8831	High Similarity	NPC477138
0.878	High Similarity	NPC253402
0.878	High Similarity	NPC159168
0.8765	High Similarity	NPC242350
0.8734	High Similarity	NPC477924
0.8734	High Similarity	NPC471798
0.8734	High Similarity	NPC472805
0.8734	High Similarity	NPC90979
0.8718	High Similarity	NPC138374
0.8718	High Similarity	NPC291503
0.8718	High Similarity	NPC34700
0.8701	High Similarity	NPC182717
0.8701	High Similarity	NPC471799
0.869	High Similarity	NPC237344
0.8642	High Similarity	NPC295131
0.8621	High Similarity	NPC301244
0.8571	High Similarity	NPC110799
0.8571	High Similarity	NPC242001
0.8537	High Similarity	NPC116202
0.85	High Similarity	NPC91594
0.8488	Intermediate Similarity	NPC470542
0.8481	Intermediate Similarity	NPC477923
0.8481	Intermediate Similarity	NPC66566
0.8462	Intermediate Similarity	NPC68443
0.8452	Intermediate Similarity	NPC474493
0.8442	Intermediate Similarity	NPC145498
0.8434	Intermediate Similarity	NPC304285
0.8434	Intermediate Similarity	NPC248886
0.8434	Intermediate Similarity	NPC20853
0.8434	Intermediate Similarity	NPC201852
0.8395	Intermediate Similarity	NPC186191
0.8395	Intermediate Similarity	NPC318136
0.8395	Intermediate Similarity	NPC76931
0.8395	Intermediate Similarity	NPC275910
0.8395	Intermediate Similarity	NPC307965
0.8395	Intermediate Similarity	NPC18603
0.8395	Intermediate Similarity	NPC205455
0.8395	Intermediate Similarity	NPC148977
0.8375	Intermediate Similarity	NPC477925
0.8375	Intermediate Similarity	NPC274079
0.8375	Intermediate Similarity	NPC265588
0.8352	Intermediate Similarity	NPC21728
0.8333	Intermediate Similarity	NPC470384
0.8333	Intermediate Similarity	NPC167706
0.8313	Intermediate Similarity	NPC476646
0.8295	Intermediate Similarity	NPC126369
0.8295	Intermediate Similarity	NPC470589
0.8295	Intermediate Similarity	NPC111110
0.8293	Intermediate Similarity	NPC472463
0.8276	Intermediate Similarity	NPC2158
0.8272	Intermediate Similarity	NPC470758
0.8272	Intermediate Similarity	NPC214570
0.8272	Intermediate Similarity	NPC470711
0.8256	Intermediate Similarity	NPC24277
0.8256	Intermediate Similarity	NPC213412
0.8242	Intermediate Similarity	NPC9487
0.8242	Intermediate Similarity	NPC88847
0.8235	Intermediate Similarity	NPC205845
0.8235	Intermediate Similarity	NPC209802
0.8235	Intermediate Similarity	NPC231310
0.8235	Intermediate Similarity	NPC53385
0.8235	Intermediate Similarity	NPC238485
0.8228	Intermediate Similarity	NPC211009
0.8214	Intermediate Similarity	NPC101462
0.8214	Intermediate Similarity	NPC30166
0.8214	Intermediate Similarity	NPC202389
0.8205	Intermediate Similarity	NPC92801
0.8193	Intermediate Similarity	NPC236237
0.8193	Intermediate Similarity	NPC96362
0.8193	Intermediate Similarity	NPC322313
0.8193	Intermediate Similarity	NPC287749
0.8193	Intermediate Similarity	NPC102253
0.8182	Intermediate Similarity	NPC263393
0.8182	Intermediate Similarity	NPC143232
0.8182	Intermediate Similarity	NPC274330
0.8182	Intermediate Similarity	NPC208999
0.8182	Intermediate Similarity	NPC187785
0.8182	Intermediate Similarity	NPC130520
0.8182	Intermediate Similarity	NPC95246
0.8182	Intermediate Similarity	NPC293048
0.8182	Intermediate Similarity	NPC259875
0.8182	Intermediate Similarity	NPC474972
0.8182	Intermediate Similarity	NPC474686
0.8182	Intermediate Similarity	NPC216460
0.8182	Intermediate Similarity	NPC198664
0.8182	Intermediate Similarity	NPC61543
0.8182	Intermediate Similarity	NPC234346
0.8182	Intermediate Similarity	NPC225585
0.8182	Intermediate Similarity	NPC161751
0.8182	Intermediate Similarity	NPC127689
0.8182	Intermediate Similarity	NPC32055
0.8182	Intermediate Similarity	NPC59263
0.8182	Intermediate Similarity	NPC270768
0.8182	Intermediate Similarity	NPC121798
0.8171	Intermediate Similarity	NPC11908
0.8171	Intermediate Similarity	NPC285761
0.8171	Intermediate Similarity	NPC167037
0.8171	Intermediate Similarity	NPC167891
0.8171	Intermediate Similarity	NPC138621
0.8171	Intermediate Similarity	NPC6978
0.8171	Intermediate Similarity	NPC83351
0.8171	Intermediate Similarity	NPC244385
0.8161	Intermediate Similarity	NPC271967
0.8161	Intermediate Similarity	NPC470620
0.8161	Intermediate Similarity	NPC73064
0.8161	Intermediate Similarity	NPC71507
0.8148	Intermediate Similarity	NPC470749
0.8148	Intermediate Similarity	NPC134330
0.8148	Intermediate Similarity	NPC73875
0.8148	Intermediate Similarity	NPC240604
0.8148	Intermediate Similarity	NPC321016
0.8148	Intermediate Similarity	NPC107059
0.8148	Intermediate Similarity	NPC46160
0.8148	Intermediate Similarity	NPC202642
0.8148	Intermediate Similarity	NPC300324
0.8148	Intermediate Similarity	NPC129165
0.8148	Intermediate Similarity	NPC470362
0.8148	Intermediate Similarity	NPC237460
0.8148	Intermediate Similarity	NPC113733
0.8148	Intermediate Similarity	NPC189883
0.8148	Intermediate Similarity	NPC321381
0.814	Intermediate Similarity	NPC133954
0.814	Intermediate Similarity	NPC477578
0.814	Intermediate Similarity	NPC191965
0.8132	Intermediate Similarity	NPC32118
0.8118	Intermediate Similarity	NPC309309
0.8118	Intermediate Similarity	NPC52108
0.8118	Intermediate Similarity	NPC291999
0.8118	Intermediate Similarity	NPC474789
0.8111	Intermediate Similarity	NPC474806
0.8111	Intermediate Similarity	NPC211230
0.8111	Intermediate Similarity	NPC229281
0.8111	Intermediate Similarity	NPC133579
0.8105	Intermediate Similarity	NPC99627
0.8105	Intermediate Similarity	NPC473129
0.8101	Intermediate Similarity	NPC301226
0.8095	Intermediate Similarity	NPC470383
0.8095	Intermediate Similarity	NPC249423
0.8095	Intermediate Similarity	NPC6707
0.8095	Intermediate Similarity	NPC142163
0.8095	Intermediate Similarity	NPC474531
0.809	Intermediate Similarity	NPC471432
0.809	Intermediate Similarity	NPC77796
0.809	Intermediate Similarity	NPC130278
0.809	Intermediate Similarity	NPC476226
0.809	Intermediate Similarity	NPC92885
0.809	Intermediate Similarity	NPC471433
0.8077	Intermediate Similarity	NPC476431
0.8077	Intermediate Similarity	NPC210323
0.8072	Intermediate Similarity	NPC273410
0.8072	Intermediate Similarity	NPC1319
0.8072	Intermediate Similarity	NPC80530
0.8068	Intermediate Similarity	NPC470629
0.8068	Intermediate Similarity	NPC181225
0.8068	Intermediate Similarity	NPC290690
0.8068	Intermediate Similarity	NPC474512
0.8068	Intermediate Similarity	NPC182797
0.8068	Intermediate Similarity	NPC17733
0.8068	Intermediate Similarity	NPC52169
0.8068	Intermediate Similarity	NPC473242
0.8052	Intermediate Similarity	NPC197805
0.8049	Intermediate Similarity	NPC130136
0.8049	Intermediate Similarity	NPC155986
0.8049	Intermediate Similarity	NPC198968
0.8049	Intermediate Similarity	NPC318495
0.8046	Intermediate Similarity	NPC475862
0.8046	Intermediate Similarity	NPC235341

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 NPC82538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1458
0.2-0.3	3996
0.3-0.4	2438
0.4-0.5	689
0.5-0.6	211
0.6-0.7	146
0.7-0.8	28
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8987	High Similarity	NPD7645	Phase 2
0.8193	Intermediate Similarity	NPD7525	Registered
0.8025	Intermediate Similarity	NPD6942	Approved
0.8025	Intermediate Similarity	NPD8264	Approved
0.8025	Intermediate Similarity	NPD7339	Approved
0.7927	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7515	Phase 2
0.7683	Intermediate Similarity	NPD6924	Approved
0.7683	Intermediate Similarity	NPD6926	Approved
0.7654	Intermediate Similarity	NPD7150	Approved
0.7654	Intermediate Similarity	NPD7152	Approved
0.7654	Intermediate Similarity	NPD7151	Approved
0.7531	Intermediate Similarity	NPD7143	Approved
0.7531	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD6933	Approved
0.7447	Intermediate Similarity	NPD7748	Approved
0.7442	Intermediate Similarity	NPD6929	Approved
0.7416	Intermediate Similarity	NPD4786	Approved
0.7412	Intermediate Similarity	NPD6932	Approved
0.7407	Intermediate Similarity	NPD6923	Approved
0.7407	Intermediate Similarity	NPD6922	Approved
0.7386	Intermediate Similarity	NPD3667	Approved
0.7356	Intermediate Similarity	NPD6930	Phase 2
0.7356	Intermediate Similarity	NPD6931	Approved
0.7356	Intermediate Similarity	NPD7509	Discontinued
0.7326	Intermediate Similarity	NPD7145	Approved
0.7303	Intermediate Similarity	NPD6695	Phase 3
0.7262	Intermediate Similarity	NPD4785	Approved
0.7262	Intermediate Similarity	NPD4784	Approved
0.7253	Intermediate Similarity	NPD3618	Phase 1
0.7234	Intermediate Similarity	NPD6079	Approved
0.7234	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7902	Approved
0.7209	Intermediate Similarity	NPD6925	Approved
0.7209	Intermediate Similarity	NPD5776	Phase 2
0.7204	Intermediate Similarity	NPD5328	Approved
0.7204	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD4748	Discontinued
0.7159	Intermediate Similarity	NPD7514	Phase 3
0.7126	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6902	Approved
0.7045	Intermediate Similarity	NPD6683	Phase 2
0.7024	Intermediate Similarity	NPD4243	Approved
0.7021	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6101	Approved
0.6989	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7524	Approved
0.6989	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6893	Approved
0.6939	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5221	Approved
0.6939	Remote Similarity	NPD5222	Approved
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.69	Remote Similarity	NPD5286	Approved
0.69	Remote Similarity	NPD4696	Approved
0.69	Remote Similarity	NPD5285	Approved
0.6889	Remote Similarity	NPD6898	Phase 1
0.6882	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD4755	Approved
0.6869	Remote Similarity	NPD5173	Approved
0.6848	Remote Similarity	NPD3666	Approved
0.6848	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD3665	Phase 1
0.6804	Remote Similarity	NPD6399	Phase 3
0.6804	Remote Similarity	NPD4202	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6786	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4697	Phase 3
0.6765	Remote Similarity	NPD5211	Phase 2
0.6765	Remote Similarity	NPD5225	Approved
0.6765	Remote Similarity	NPD5226	Approved
0.6765	Remote Similarity	NPD5224	Approved
0.6765	Remote Similarity	NPD4633	Approved
0.6733	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD7640	Approved
0.6733	Remote Similarity	NPD4700	Approved
0.6701	Remote Similarity	NPD7087	Discontinued
0.6699	Remote Similarity	NPD5175	Approved
0.6699	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD5141	Approved
0.6634	Remote Similarity	NPD5290	Discontinued
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD6899	Approved
0.6604	Remote Similarity	NPD6881	Approved
0.6598	Remote Similarity	NPD7136	Phase 2
0.6593	Remote Similarity	NPD4695	Discontinued
0.6591	Remote Similarity	NPD4190	Phase 3
0.6591	Remote Similarity	NPD5275	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6531	Remote Similarity	NPD8034	Phase 2
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD7637	Suspended
0.6509	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD4629	Approved
0.65	Remote Similarity	NPD5210	Approved
0.6481	Remote Similarity	NPD7290	Approved
0.6481	Remote Similarity	NPD7102	Approved
0.6481	Remote Similarity	NPD6883	Approved
0.6471	Remote Similarity	NPD4225	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD4730	Approved
0.6449	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD7115	Discovery
0.6422	Remote Similarity	NPD6617	Approved
0.6422	Remote Similarity	NPD8130	Phase 1
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6869	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD4767	Approved
0.6415	Remote Similarity	NPD4768	Approved
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD6012	Approved
0.6389	Remote Similarity	NPD6013	Approved
0.6389	Remote Similarity	NPD6014	Approved
0.6381	Remote Similarity	NPD4754	Approved
0.6373	Remote Similarity	NPD6083	Phase 2
0.6373	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD4694	Approved
0.6354	Remote Similarity	NPD5280	Approved
0.6354	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7503	Approved
0.6341	Remote Similarity	NPD368	Approved
0.633	Remote Similarity	NPD5248	Approved
0.633	Remote Similarity	NPD5251	Approved
0.633	Remote Similarity	NPD5250	Approved
0.633	Remote Similarity	NPD4634	Approved
0.633	Remote Similarity	NPD5249	Phase 3
0.633	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD5128	Approved
0.6296	Remote Similarity	NPD5168	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6289	Remote Similarity	NPD3573	Approved
0.6277	Remote Similarity	NPD4223	Phase 3
0.6277	Remote Similarity	NPD4221	Approved
0.6275	Remote Similarity	NPD7614	Phase 1
0.6273	Remote Similarity	NPD5217	Approved
0.6273	Remote Similarity	NPD5215	Approved
0.6273	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5329	Approved
0.6211	Remote Similarity	NPD4788	Approved
0.6207	Remote Similarity	NPD8033	Approved
0.6204	Remote Similarity	NPD6412	Phase 2
0.619	Remote Similarity	NPD4159	Approved
0.6186	Remote Similarity	NPD7334	Approved
0.6186	Remote Similarity	NPD4623	Approved
0.6186	Remote Similarity	NPD4519	Discontinued
0.6186	Remote Similarity	NPD7146	Approved
0.6186	Remote Similarity	NPD6684	Approved
0.6186	Remote Similarity	NPD6409	Approved
0.6186	Remote Similarity	NPD5330	Approved
0.6186	Remote Similarity	NPD5690	Phase 2
0.6186	Remote Similarity	NPD7521	Approved
0.6182	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5169	Approved
0.6182	Remote Similarity	NPD5135	Approved
0.618	Remote Similarity	NPD4732	Discontinued
0.6176	Remote Similarity	NPD5695	Phase 3
0.6162	Remote Similarity	NPD6051	Approved
0.6154	Remote Similarity	NPD6117	Approved
0.6146	Remote Similarity	NPD4197	Approved
0.614	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4787	Phase 1
0.6132	Remote Similarity	NPD7632	Discontinued
0.6126	Remote Similarity	NPD5127	Approved
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4219	Approved
0.6121	Remote Similarity	NPD8377	Approved
0.6121	Remote Similarity	NPD8294	Approved
0.6102	Remote Similarity	NPD8328	Phase 3
0.6087	Remote Similarity	NPD7327	Approved
0.6087	Remote Similarity	NPD7328	Approved
0.6087	Remote Similarity	NPD6116	Phase 1
0.6082	Remote Similarity	NPD1696	Phase 3
0.6068	Remote Similarity	NPD8380	Approved
0.6068	Remote Similarity	NPD8296	Approved
0.6068	Remote Similarity	NPD8378	Approved
0.6068	Remote Similarity	NPD8335	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