NPASS Compound

Structure

CID275671 OpenBabel06191716082D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.4282 -3.1301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2677 -5.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5429 -6.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8450 2.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7183 1.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5367 -2.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5366 0.5204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7335 -4.5797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0348 -3.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 0.9763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2266 -1.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3861 -5.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2265 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 -1.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 -1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3822 -2.9273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3822 -1.9520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9763 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6911 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6899 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6899 0.9763 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3401 -5.1016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8450 1.4644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5367 -1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5366 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8456 -0.4881 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 2.5560 -0.4999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5560 1.4761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6415 -4.1741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 27 1 1 0 0 0 20 26 1 0 0 0 0 20 30 1 1 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 30 1 6 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 27 28 1 1 0 0 0 28 7 1 6 0 0 0 29 30 1 6 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	5.121
LogD:	4.38
LogS:	-4.304
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	6.045
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.972
MDCK Permeability:	1.579527997819241e-05
Pgp-inhibitor:	0.096
Pgp-substrate:	0.155
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.252
Plasma Protein Binding (PPB):	95.68616485595703%
Volume Distribution (VD):	1.009
Pgp-substrate:	2.8956079483032227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.713
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	2.787
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.547
Maximum Recommended Daily Dose:	0.229
Skin Sensitization:	0.856
Carcinogencity:	0.361
Eye Corrosion:	0.005
Eye Irritation:	0.017
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC275671

Natural Product ID:	NPC275671
*Common Name:**	AAUDVCPRPMQVGQ-NLTJIPSISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AAUDVCPRPMQVGQ-NLTJIPSISA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(9-8-13-25(2,3)34)19-12-14-28(7)21-11-10-20-26(4,5)23(32)22(31)24(33)30(20)17-29(21,30)16-15-27(19,28)6/h8,13,18-24,31-34H,9-12,14-17H2,1-7H3/b13-8+/t18-,19-,20+,21+,22+,23+,24+,27-,28+,29+,30-/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)[C@@H](O)[C@@H](O)[C@@H](C2(C)C)O)C)C/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254751
PubChem CID:	24770735
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177010]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24891	Elmerina caryae	Species	Aporpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3693	Calpurnia aurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	10300.0	nM	PMID[515078]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	34700.0	nM	PMID[515078]

☑ 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 NPC275671 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	199
0.1-0.2	1649
0.2-0.3	5646
0.3-0.4	14486
0.4-0.5	9293
0.5-0.6	5567
0.6-0.7	4592
0.7-0.8	1126
0.8-0.85	95
0.85-0.9	39
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9186	High Similarity	NPC269058
0.9186	High Similarity	NPC71520
0.9101	High Similarity	NPC41554
0.9101	High Similarity	NPC97404
0.9091	High Similarity	NPC109744
0.907	High Similarity	NPC470360
0.9059	High Similarity	NPC82623
0.9022	High Similarity	NPC477226
0.8989	High Similarity	NPC80561
0.8989	High Similarity	NPC204188
0.8989	High Similarity	NPC475751
0.8989	High Similarity	NPC3345
0.8989	High Similarity	NPC291484
0.8989	High Similarity	NPC11216
0.8989	High Similarity	NPC473956
0.8989	High Similarity	NPC329596
0.8977	High Similarity	NPC67872
0.8977	High Similarity	NPC133588
0.8966	High Similarity	NPC299068
0.8876	High Similarity	NPC470361
0.8864	High Similarity	NPC474657
0.8864	High Similarity	NPC186145
0.8837	High Similarity	NPC113978
0.8837	High Similarity	NPC134481
0.8764	High Similarity	NPC474668
0.8764	High Similarity	NPC475664
0.875	High Similarity	NPC6391
0.875	High Similarity	NPC94462
0.875	High Similarity	NPC6605
0.875	High Similarity	NPC139724
0.875	High Similarity	NPC261266
0.8721	High Similarity	NPC296701
0.8721	High Similarity	NPC218616
0.871	High Similarity	NPC288970
0.8667	High Similarity	NPC138974
0.8652	High Similarity	NPC470620
0.8621	High Similarity	NPC211135
0.8621	High Similarity	NPC85095
0.8621	High Similarity	NPC216420
0.8621	High Similarity	NPC207013
0.8617	High Similarity	NPC476040
0.8617	High Similarity	NPC476021
0.8617	High Similarity	NPC474994
0.8587	High Similarity	NPC310013
0.8556	High Similarity	NPC4574
0.8556	High Similarity	NPC475605
0.8556	High Similarity	NPC212596
0.8556	High Similarity	NPC280556
0.8539	High Similarity	NPC201273
0.8523	High Similarity	NPC185568
0.8523	High Similarity	NPC205845
0.8511	High Similarity	NPC210717
0.8511	High Similarity	NPC103165
0.8511	High Similarity	NPC471903
0.8506	High Similarity	NPC30166
0.8495	Intermediate Similarity	NPC65402
0.8495	Intermediate Similarity	NPC127718
0.8495	Intermediate Similarity	NPC477605
0.8488	Intermediate Similarity	NPC13554
0.8462	Intermediate Similarity	NPC259875
0.8462	Intermediate Similarity	NPC101886
0.8462	Intermediate Similarity	NPC187785
0.8444	Intermediate Similarity	NPC304083
0.8421	Intermediate Similarity	NPC476893
0.8421	Intermediate Similarity	NPC261807
0.8421	Intermediate Similarity	NPC316604
0.8409	Intermediate Similarity	NPC141941
0.8409	Intermediate Similarity	NPC474634
0.8409	Intermediate Similarity	NPC317458
0.8409	Intermediate Similarity	NPC193870
0.8409	Intermediate Similarity	NPC470558
0.8404	Intermediate Similarity	NPC8774
0.8391	Intermediate Similarity	NPC249423
0.8387	Intermediate Similarity	NPC27531
0.837	Intermediate Similarity	NPC295668
0.8351	Intermediate Similarity	NPC476896
0.8333	Intermediate Similarity	NPC102426
0.8333	Intermediate Similarity	NPC300179
0.8333	Intermediate Similarity	NPC476895
0.8333	Intermediate Similarity	NPC152808
0.8333	Intermediate Similarity	NPC121981
0.8333	Intermediate Similarity	NPC293287
0.8316	Intermediate Similarity	NPC98457
0.8316	Intermediate Similarity	NPC227583
0.8316	Intermediate Similarity	NPC12103
0.8316	Intermediate Similarity	NPC72204
0.8315	Intermediate Similarity	NPC15534
0.8315	Intermediate Similarity	NPC475798
0.8315	Intermediate Similarity	NPC127606
0.8298	Intermediate Similarity	NPC144202
0.8295	Intermediate Similarity	NPC50964
0.8295	Intermediate Similarity	NPC87489
0.8295	Intermediate Similarity	NPC49964
0.8295	Intermediate Similarity	NPC101462
0.8283	Intermediate Similarity	NPC201763
0.8276	Intermediate Similarity	NPC236237
0.8276	Intermediate Similarity	NPC102253
0.8276	Intermediate Similarity	NPC322313
0.8276	Intermediate Similarity	NPC236112
0.8276	Intermediate Similarity	NPC471266
0.8276	Intermediate Similarity	NPC95124
0.8261	Intermediate Similarity	NPC105495
0.8256	Intermediate Similarity	NPC65897
0.8256	Intermediate Similarity	NPC85346
0.8256	Intermediate Similarity	NPC285761
0.8256	Intermediate Similarity	NPC302041
0.8256	Intermediate Similarity	NPC472342
0.8256	Intermediate Similarity	NPC11908
0.8256	Intermediate Similarity	NPC31828
0.8242	Intermediate Similarity	NPC477600
0.8242	Intermediate Similarity	NPC149224
0.8222	Intermediate Similarity	NPC318390
0.8202	Intermediate Similarity	NPC477818
0.8202	Intermediate Similarity	NPC185605
0.8202	Intermediate Similarity	NPC320548
0.8202	Intermediate Similarity	NPC110778
0.8191	Intermediate Similarity	NPC307776
0.8182	Intermediate Similarity	NPC264245
0.8182	Intermediate Similarity	NPC209620
0.8182	Intermediate Similarity	NPC474531
0.8182	Intermediate Similarity	NPC23852
0.8182	Intermediate Similarity	NPC471270
0.8182	Intermediate Similarity	NPC470383
0.8172	Intermediate Similarity	NPC192437
0.8172	Intermediate Similarity	NPC270511
0.8172	Intermediate Similarity	NPC14380
0.8172	Intermediate Similarity	NPC470390
0.8172	Intermediate Similarity	NPC245410
0.8163	Intermediate Similarity	NPC289670
0.8161	Intermediate Similarity	NPC30986
0.8161	Intermediate Similarity	NPC80530
0.8161	Intermediate Similarity	NPC273410
0.8161	Intermediate Similarity	NPC209430
0.814	Intermediate Similarity	NPC470758
0.814	Intermediate Similarity	NPC331618
0.814	Intermediate Similarity	NPC470711
0.814	Intermediate Similarity	NPC257191
0.8132	Intermediate Similarity	NPC125399
0.8118	Intermediate Similarity	NPC103822
0.8111	Intermediate Similarity	NPC231310
0.8111	Intermediate Similarity	NPC255882
0.8111	Intermediate Similarity	NPC474493
0.8111	Intermediate Similarity	NPC474047
0.8111	Intermediate Similarity	NPC470077
0.809	Intermediate Similarity	NPC7988
0.8085	Intermediate Similarity	NPC114389
0.8085	Intermediate Similarity	NPC210268
0.8068	Intermediate Similarity	NPC209944
0.8068	Intermediate Similarity	NPC164840
0.8068	Intermediate Similarity	NPC236707
0.8068	Intermediate Similarity	NPC241290
0.8068	Intermediate Similarity	NPC234193
0.8065	Intermediate Similarity	NPC477606
0.8046	Intermediate Similarity	NPC301707
0.8046	Intermediate Similarity	NPC6978
0.8046	Intermediate Similarity	NPC148977
0.8046	Intermediate Similarity	NPC244385
0.8046	Intermediate Similarity	NPC312328
0.8046	Intermediate Similarity	NPC167037
0.8046	Intermediate Similarity	NPC138621
0.8046	Intermediate Similarity	NPC147993
0.8043	Intermediate Similarity	NPC476948
0.8023	Intermediate Similarity	NPC470749
0.8023	Intermediate Similarity	NPC237460
0.8023	Intermediate Similarity	NPC91573
0.8022	Intermediate Similarity	NPC266511
0.8022	Intermediate Similarity	NPC274448
0.8022	Intermediate Similarity	NPC22133
0.8021	Intermediate Similarity	NPC476894
0.8	Intermediate Similarity	NPC137461
0.8	Intermediate Similarity	NPC232023
0.8	Intermediate Similarity	NPC475789
0.8	Intermediate Similarity	NPC477978
0.8	Intermediate Similarity	NPC119379
0.8	Intermediate Similarity	NPC476304
0.798	Intermediate Similarity	NPC476897
0.7979	Intermediate Similarity	NPC191323
0.7978	Intermediate Similarity	NPC476646
0.7978	Intermediate Similarity	NPC47761
0.7978	Intermediate Similarity	NPC320525
0.7961	Intermediate Similarity	NPC257082
0.7957	Intermediate Similarity	NPC473436
0.7955	Intermediate Similarity	NPC328714
0.7955	Intermediate Similarity	NPC472463
0.7955	Intermediate Similarity	NPC28862
0.7955	Intermediate Similarity	NPC84694
0.7955	Intermediate Similarity	NPC80297
0.7955	Intermediate Similarity	NPC109546
0.7955	Intermediate Similarity	NPC476316
0.7955	Intermediate Similarity	NPC472742
0.7955	Intermediate Similarity	NPC143182
0.7955	Intermediate Similarity	NPC116119
0.7955	Intermediate Similarity	NPC47982
0.7955	Intermediate Similarity	NPC475727
0.7955	Intermediate Similarity	NPC81306
0.7941	Intermediate Similarity	NPC263729
0.7941	Intermediate Similarity	NPC477916
0.7938	Intermediate Similarity	NPC276103
0.7938	Intermediate Similarity	NPC54248
0.7938	Intermediate Similarity	NPC195366

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 NPC275671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1776
0.2-0.3	4368
0.3-0.4	1966
0.4-0.5	459
0.5-0.6	204
0.6-0.7	170
0.7-0.8	26
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
0.8276	Intermediate Similarity	NPD7525	Registered
0.8043	Intermediate Similarity	NPD7524	Approved
0.7978	Intermediate Similarity	NPD6902	Approved
0.7865	Intermediate Similarity	NPD7514	Phase 3
0.7865	Intermediate Similarity	NPD6930	Phase 2
0.7865	Intermediate Similarity	NPD6931	Approved
0.7802	Intermediate Similarity	NPD6695	Phase 3
0.7753	Intermediate Similarity	NPD6929	Approved
0.7717	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7332	Phase 2
0.766	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7145	Approved
0.7529	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6925	Approved
0.7528	Intermediate Similarity	NPD6932	Approved
0.7528	Intermediate Similarity	NPD5776	Phase 2
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD7339	Approved
0.7474	Intermediate Similarity	NPD7750	Discontinued
0.7447	Intermediate Similarity	NPD6893	Approved
0.7416	Intermediate Similarity	NPD6933	Approved
0.7363	Intermediate Similarity	NPD7645	Phase 2
0.7353	Intermediate Similarity	NPD7639	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7255	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6898	Phase 1
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7174	Intermediate Similarity	NPD6683	Phase 2
0.7172	Intermediate Similarity	NPD7087	Discontinued
0.7168	Intermediate Similarity	NPD7516	Approved
0.708	Intermediate Similarity	NPD7327	Approved
0.708	Intermediate Similarity	NPD7328	Approved
0.7065	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD4784	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.6991	Remote Similarity	NPD7115	Discovery
0.6979	Remote Similarity	NPD4786	Approved
0.697	Remote Similarity	NPD5328	Approved
0.6966	Remote Similarity	NPD7150	Approved
0.6966	Remote Similarity	NPD7151	Approved
0.6966	Remote Similarity	NPD7152	Approved
0.6966	Remote Similarity	NPD4243	Approved
0.6952	Remote Similarity	NPD4159	Approved
0.6916	Remote Similarity	NPD5141	Approved
0.6909	Remote Similarity	NPD4634	Approved
0.6897	Remote Similarity	NPD8379	Approved
0.6897	Remote Similarity	NPD8335	Approved
0.6897	Remote Similarity	NPD8296	Approved
0.6897	Remote Similarity	NPD8378	Approved
0.6897	Remote Similarity	NPD8380	Approved
0.6857	Remote Similarity	NPD5286	Approved
0.6857	Remote Similarity	NPD5285	Approved
0.6857	Remote Similarity	NPD4696	Approved
0.6854	Remote Similarity	NPD7143	Approved
0.6854	Remote Similarity	NPD7144	Approved
0.6837	Remote Similarity	NPD3618	Phase 1
0.6827	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD8377	Approved
0.681	Remote Similarity	NPD8294	Approved
0.6792	Remote Similarity	NPD5344	Discontinued
0.6771	Remote Similarity	NPD3667	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6752	Remote Similarity	NPD8033	Approved
0.6742	Remote Similarity	NPD6922	Approved
0.6742	Remote Similarity	NPD6923	Approved
0.6739	Remote Similarity	NPD8264	Approved
0.6737	Remote Similarity	NPD4748	Discontinued
0.6737	Remote Similarity	NPD7509	Discontinued
0.6735	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7136	Phase 2
0.6731	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5221	Approved
0.6731	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7632	Discontinued
0.6729	Remote Similarity	NPD5224	Approved
0.6729	Remote Similarity	NPD5225	Approved
0.6729	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD4633	Approved
0.6698	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD4753	Phase 2
0.6632	Remote Similarity	NPD4195	Approved
0.661	Remote Similarity	NPD7503	Approved
0.6604	Remote Similarity	NPD4225	Approved
0.6579	Remote Similarity	NPD4632	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD5275	Approved
0.6559	Remote Similarity	NPD4190	Phase 3
0.6545	Remote Similarity	NPD7128	Approved
0.6545	Remote Similarity	NPD5739	Approved
0.6545	Remote Similarity	NPD6675	Approved
0.6545	Remote Similarity	NPD6402	Approved
0.6529	Remote Similarity	NPD7507	Approved
0.6526	Remote Similarity	NPD6697	Approved
0.6526	Remote Similarity	NPD6118	Approved
0.6526	Remote Similarity	NPD6115	Approved
0.6526	Remote Similarity	NPD6114	Approved
0.6505	Remote Similarity	NPD7515	Phase 2
0.6504	Remote Similarity	NPD7319	Approved
0.6491	Remote Similarity	NPD8297	Approved
0.6486	Remote Similarity	NPD5697	Approved
0.6484	Remote Similarity	NPD4787	Phase 1
0.6476	Remote Similarity	NPD5210	Approved
0.6476	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD6051	Approved
0.6465	Remote Similarity	NPD3665	Phase 1
0.6465	Remote Similarity	NPD3133	Approved
0.6465	Remote Similarity	NPD3666	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD4730	Approved
0.6429	Remote Similarity	NPD4729	Approved
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6869	Approved
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6650	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD4767	Approved
0.6396	Remote Similarity	NPD6640	Phase 3
0.6396	Remote Similarity	NPD4768	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD7741	Discontinued
0.6387	Remote Similarity	NPD6319	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD4788	Approved
0.6355	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD6083	Phase 2
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6882	Approved
0.6346	Remote Similarity	NPD8035	Phase 2
0.6346	Remote Similarity	NPD8034	Phase 2
0.6339	Remote Similarity	NPD5701	Approved
0.6339	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5248	Approved
0.6316	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5250	Approved
0.6316	Remote Similarity	NPD5247	Approved
0.6316	Remote Similarity	NPD6117	Approved
0.6316	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD5251	Approved
0.63	Remote Similarity	NPD3668	Phase 3
0.6296	Remote Similarity	NPD5290	Discontinued
0.6283	Remote Similarity	NPD5128	Approved
0.6283	Remote Similarity	NPD6011	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6271	Remote Similarity	NPD6009	Approved
0.6263	Remote Similarity	NPD4221	Approved
0.6263	Remote Similarity	NPD4223	Phase 3
0.6261	Remote Similarity	NPD5217	Approved
0.6261	Remote Similarity	NPD5215	Approved
0.6261	Remote Similarity	NPD5216	Approved
0.625	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD6059	Approved
0.6238	Remote Similarity	NPD5329	Approved
0.6237	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7748	Approved
0.6224	Remote Similarity	NPD4822	Approved
0.6224	Remote Similarity	NPD4820	Approved
0.6224	Remote Similarity	NPD4821	Approved
0.6224	Remote Similarity	NPD4819	Approved
0.6211	Remote Similarity	NPD3703	Phase 2
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6179	Remote Similarity	NPD7492	Approved
0.6176	Remote Similarity	NPD5279	Phase 3
0.6176	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4519	Discontinued
0.6176	Remote Similarity	NPD4623	Approved
0.6174	Remote Similarity	NPD5169	Approved
0.6174	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5135	Approved
0.617	Remote Similarity	NPD4732	Discontinued
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD8133	Approved
0.6148	Remote Similarity	NPD5988	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