NPASS Compound

Structure

NPC473396 OpenBabel07101718292D 37 42 0 0 1 0 0 0 0 0999 V2000 -6.6549 4.6028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 3.4135 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 -5.6315 2.4964 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 1.7321 0.0000 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 3.0000 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 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2704 3.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1013 4.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -4.2923 3.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.1877 4.4727 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7682 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7704 4.1363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4677 3.4829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -5.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5603 2.3340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4040 3.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 3.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1985 3.7527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 24 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 23 1 0 0 0 0 13 9 1 1 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 25 1 6 0 0 0 15 24 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 12 1 1 0 0 0 17 37 1 0 0 0 0 18 28 1 1 0 0 0 18 29 1 0 0 0 0 19 25 1 0 0 0 0 19 30 2 0 0 0 0 20 28 1 6 0 0 0 20 31 1 0 0 0 0 21 27 1 1 0 0 0 21 32 1 0 0 0 0 22 26 1 0 0 0 0 22 33 2 0 0 0 0 22 37 1 0 0 0 0 23 26 1 1 0 0 0 24 27 1 1 0 0 0 25 28 1 6 0 0 0 26 4 1 1 0 0 0 26 34 1 0 0 0 0 27 35 1 1 0 0 0 28 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.23
Volume:	519.129
LogP:	2.212
LogD:	2.472
LogS:	-4.309
# Rotatable Bonds:	1
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	6.47
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.297
MDCK Permeability:	8.879764209268615e-06
Pgp-inhibitor:	0.37
Pgp-substrate:	0.478
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.357

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	63.86500549316406%
Volume Distribution (VD):	0.591
Pgp-substrate:	20.5053653717041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.715
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.761

ADMET: Excretion

Clearance (CL):	3.232
Half-life (T1/2):	0.691

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.775
Skin Sensitization:	0.344
Carcinogencity:	0.535
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC473396

Natural Product ID:	NPC473396
*Common Name:**	Anomanolide D
IUPAC Name:	(1R,4R,5R)-7-[(4S,5R,6S,8S,9S,10R,13S,14S,16R,17S)-6-chloro-4,5,16,17-tetrahydroxy-10,13-dimethyl-1-oxo-4,6,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-4-hydroxy-4,5-dimethyl-2-oxabicyclo[3.2.1]octan-3-one
Synonyms:	Anomanolide D
Standard InCHIKey:	SHCLKNUPAXEEPB-XVCVBXNTSA-N
Standard InCHI:	InChI=1S/C28H39ClO8/c1-23-11-16(17(12-23)37-22(33)26(23,4)34)27(35)21(32)10-15-13-9-18(29)28(36)20(31)6-5-19(30)25(28,3)14(13)7-8-24(15,27)2/h5-6,13-18,20-21,31-32,34-36H,7-12H2,1-4H3/t13-,14+,15+,16?,17-,18+,20+,21-,23-,24+,25+,26+,27-,28+/m1/s1
SMILES:	O[C@@H]1C[C@@H]2[C@]([C@@]1(O)C1C[C@@]3(C[C@H]1OC(=O)[C@]3(C)O)C)(C)CC[C@H]1[C@H]2C[C@H](Cl)[C@]2([C@]1(C)C(=O)C=C[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL410742
PubChem CID:	44423065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[547807]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[547807]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[547807]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[547807]
NPT27	Others	Unspecified		IC50	=	19.03	ug.mL-1	PMID[547807]

☑ 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 NPC473396 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	317
0.1-0.2	1795
0.2-0.3	5549
0.3-0.4	9477
0.4-0.5	12216
0.5-0.6	7542
0.6-0.7	4832
0.7-0.8	943
0.8-0.85	15
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9389	High Similarity	NPC473233
0.9062	High Similarity	NPC473265
0.8923	High Similarity	NPC470880
0.8915	High Similarity	NPC470882
0.8769	High Similarity	NPC473253
0.876	High Similarity	NPC473255
0.8667	High Similarity	NPC245017
0.8657	High Similarity	NPC296617
0.8529	High Similarity	NPC130447
0.8485	Intermediate Similarity	NPC156797
0.8382	Intermediate Similarity	NPC198361
0.8231	Intermediate Similarity	NPC61520
0.8231	Intermediate Similarity	NPC473203
0.8209	Intermediate Similarity	NPC287903
0.8154	Intermediate Similarity	NPC329736
0.8106	Intermediate Similarity	NPC470921
0.8088	Intermediate Similarity	NPC231529
0.8045	Intermediate Similarity	NPC269642
0.8045	Intermediate Similarity	NPC222688
0.8	Intermediate Similarity	NPC270929
0.7985	Intermediate Similarity	NPC469789
0.7971	Intermediate Similarity	NPC471855
0.797	Intermediate Similarity	NPC46570
0.7941	Intermediate Similarity	NPC287423
0.7939	Intermediate Similarity	NPC471854
0.7926	Intermediate Similarity	NPC8369
0.791	Intermediate Similarity	NPC470265
0.791	Intermediate Similarity	NPC107493
0.791	Intermediate Similarity	NPC23786
0.7895	Intermediate Similarity	NPC109973
0.7883	Intermediate Similarity	NPC473888
0.7883	Intermediate Similarity	NPC311534
0.7883	Intermediate Similarity	NPC473620
0.7879	Intermediate Similarity	NPC251310
0.7868	Intermediate Similarity	NPC470973
0.7868	Intermediate Similarity	NPC293112
0.7863	Intermediate Similarity	NPC266728
0.7863	Intermediate Similarity	NPC49492
0.7846	Intermediate Similarity	NPC250109
0.7846	Intermediate Similarity	NPC962
0.7846	Intermediate Similarity	NPC194100
0.7836	Intermediate Similarity	NPC67569
0.7826	Intermediate Similarity	NPC471407
0.782	Intermediate Similarity	NPC475041
0.781	Intermediate Similarity	NPC305496
0.7803	Intermediate Similarity	NPC239273
0.7794	Intermediate Similarity	NPC8374
0.7794	Intermediate Similarity	NPC81736
0.7794	Intermediate Similarity	NPC172154
0.7794	Intermediate Similarity	NPC470922
0.7786	Intermediate Similarity	NPC469673
0.777	Intermediate Similarity	NPC196921
0.777	Intermediate Similarity	NPC220757
0.7761	Intermediate Similarity	NPC474370
0.7761	Intermediate Similarity	NPC79579
0.7761	Intermediate Similarity	NPC476961
0.7744	Intermediate Similarity	NPC473720
0.7744	Intermediate Similarity	NPC311554
0.7744	Intermediate Similarity	NPC257457
0.7737	Intermediate Similarity	NPC174367
0.7737	Intermediate Similarity	NPC47113
0.7737	Intermediate Similarity	NPC473635
0.773	Intermediate Similarity	NPC471234
0.773	Intermediate Similarity	NPC476823
0.7727	Intermediate Similarity	NPC148458
0.7721	Intermediate Similarity	NPC473979
0.7721	Intermediate Similarity	NPC11895
0.7721	Intermediate Similarity	NPC67251
0.7721	Intermediate Similarity	NPC120724
0.7714	Intermediate Similarity	NPC34963
0.7698	Intermediate Similarity	NPC221414
0.7698	Intermediate Similarity	NPC35109
0.7687	Intermediate Similarity	NPC264954
0.7687	Intermediate Similarity	NPC469488
0.7687	Intermediate Similarity	NPC5292
0.7687	Intermediate Similarity	NPC472933
0.7669	Intermediate Similarity	NPC122033
0.7669	Intermediate Similarity	NPC474654
0.7669	Intermediate Similarity	NPC176513
0.7669	Intermediate Similarity	NPC218970
0.7669	Intermediate Similarity	NPC287343
0.7669	Intermediate Similarity	NPC470775
0.7669	Intermediate Similarity	NPC470854
0.7669	Intermediate Similarity	NPC97908
0.7664	Intermediate Similarity	NPC476729
0.7664	Intermediate Similarity	NPC24651
0.766	Intermediate Similarity	NPC469674
0.766	Intermediate Similarity	NPC58029
0.7652	Intermediate Similarity	NPC326542
0.7652	Intermediate Similarity	NPC243354
0.7647	Intermediate Similarity	NPC88326
0.7647	Intermediate Similarity	NPC28532
0.7647	Intermediate Similarity	NPC153700
0.7647	Intermediate Similarity	NPC170538
0.7643	Intermediate Similarity	NPC173347
0.7643	Intermediate Similarity	NPC279478
0.7643	Intermediate Similarity	NPC241935
0.7634	Intermediate Similarity	NPC280782
0.7634	Intermediate Similarity	NPC207251
0.763	Intermediate Similarity	NPC474585
0.763	Intermediate Similarity	NPC472004
0.763	Intermediate Similarity	NPC476962
0.763	Intermediate Similarity	NPC112038
0.7612	Intermediate Similarity	NPC153440
0.7612	Intermediate Similarity	NPC470776
0.7612	Intermediate Similarity	NPC709
0.7612	Intermediate Similarity	NPC297179
0.7612	Intermediate Similarity	NPC50774
0.7612	Intermediate Similarity	NPC17772
0.7594	Intermediate Similarity	NPC328374
0.7594	Intermediate Similarity	NPC190286
0.7594	Intermediate Similarity	NPC40632
0.7594	Intermediate Similarity	NPC251236
0.7594	Intermediate Similarity	NPC270958
0.7594	Intermediate Similarity	NPC96312
0.7594	Intermediate Similarity	NPC474734
0.7591	Intermediate Similarity	NPC105926
0.7591	Intermediate Similarity	NPC91693
0.7591	Intermediate Similarity	NPC204812
0.7591	Intermediate Similarity	NPC18945
0.7591	Intermediate Similarity	NPC265557
0.7589	Intermediate Similarity	NPC231240
0.7589	Intermediate Similarity	NPC102316
0.7576	Intermediate Similarity	NPC7921
0.7576	Intermediate Similarity	NPC472926
0.7576	Intermediate Similarity	NPC49451
0.7576	Intermediate Similarity	NPC317210
0.7576	Intermediate Similarity	NPC73300
0.7576	Intermediate Similarity	NPC108721
0.7576	Intermediate Similarity	NPC208998
0.7576	Intermediate Similarity	NPC52634
0.7574	Intermediate Similarity	NPC471999
0.7574	Intermediate Similarity	NPC202051
0.7574	Intermediate Similarity	NPC472001
0.7574	Intermediate Similarity	NPC472000
0.7571	Intermediate Similarity	NPC473593
0.7571	Intermediate Similarity	NPC476966
0.7557	Intermediate Similarity	NPC472003
0.7556	Intermediate Similarity	NPC475520
0.7556	Intermediate Similarity	NPC475775
0.7556	Intermediate Similarity	NPC470777
0.7556	Intermediate Similarity	NPC476960
0.7556	Intermediate Similarity	NPC319570
0.7556	Intermediate Similarity	NPC476529
0.7554	Intermediate Similarity	NPC117702
0.7554	Intermediate Similarity	NPC471357
0.7554	Intermediate Similarity	NPC469757
0.7554	Intermediate Similarity	NPC152091
0.7554	Intermediate Similarity	NPC478207
0.7554	Intermediate Similarity	NPC146456
0.7538	Intermediate Similarity	NPC214644
0.7537	Intermediate Similarity	NPC470959
0.7537	Intermediate Similarity	NPC470492
0.7537	Intermediate Similarity	NPC140055
0.7537	Intermediate Similarity	NPC470171
0.7537	Intermediate Similarity	NPC476965
0.7537	Intermediate Similarity	NPC472927
0.7537	Intermediate Similarity	NPC472934
0.7537	Intermediate Similarity	NPC286528
0.7537	Intermediate Similarity	NPC20302
0.7537	Intermediate Similarity	NPC167606
0.7536	Intermediate Similarity	NPC241456
0.7536	Intermediate Similarity	NPC32868
0.7535	Intermediate Similarity	NPC316915
0.7534	Intermediate Similarity	NPC25887
0.7519	Intermediate Similarity	NPC473798
0.7519	Intermediate Similarity	NPC300051
0.7519	Intermediate Similarity	NPC147912
0.7519	Intermediate Similarity	NPC67259
0.7519	Intermediate Similarity	NPC178289
0.7519	Intermediate Similarity	NPC471398
0.7518	Intermediate Similarity	NPC213634
0.7518	Intermediate Similarity	NPC312833
0.7518	Intermediate Similarity	NPC313528
0.7518	Intermediate Similarity	NPC65858
0.75	Intermediate Similarity	NPC471172
0.75	Intermediate Similarity	NPC107338
0.75	Intermediate Similarity	NPC100267
0.75	Intermediate Similarity	NPC475524
0.75	Intermediate Similarity	NPC269530
0.75	Intermediate Similarity	NPC471406
0.75	Intermediate Similarity	NPC71348
0.75	Intermediate Similarity	NPC109607
0.75	Intermediate Similarity	NPC245094
0.7482	Intermediate Similarity	NPC15095
0.7481	Intermediate Similarity	NPC235077
0.7481	Intermediate Similarity	NPC204552
0.7481	Intermediate Similarity	NPC21326
0.7481	Intermediate Similarity	NPC118638
0.7481	Intermediate Similarity	NPC188667
0.7481	Intermediate Similarity	NPC197428
0.7465	Intermediate Similarity	NPC470185
0.7465	Intermediate Similarity	NPC100390
0.7465	Intermediate Similarity	NPC254614
0.7464	Intermediate Similarity	NPC135038
0.7464	Intermediate Similarity	NPC27363
0.7464	Intermediate Similarity	NPC43252
0.7463	Intermediate Similarity	NPC474046
0.7463	Intermediate Similarity	NPC134869
0.7463	Intermediate Similarity	NPC235539

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 NPC473396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	1933
0.2-0.3	4110
0.3-0.4	1866
0.4-0.5	581
0.5-0.6	226
0.6-0.7	121
0.7-0.8	63
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD6336	Discontinued
0.8231	Intermediate Similarity	NPD7100	Approved
0.8231	Intermediate Similarity	NPD7101	Approved
0.803	Intermediate Similarity	NPD6319	Approved
0.7984	Intermediate Similarity	NPD4632	Approved
0.797	Intermediate Similarity	NPD5983	Phase 2
0.7883	Intermediate Similarity	NPD6033	Approved
0.7829	Intermediate Similarity	NPD5215	Approved
0.7829	Intermediate Similarity	NPD5216	Approved
0.7829	Intermediate Similarity	NPD5217	Approved
0.781	Intermediate Similarity	NPD7078	Approved
0.7794	Intermediate Similarity	NPD7492	Approved
0.7786	Intermediate Similarity	NPD5167	Approved
0.777	Intermediate Similarity	NPD5956	Approved
0.7761	Intermediate Similarity	NPD6054	Approved
0.7754	Intermediate Similarity	NPD7736	Approved
0.7744	Intermediate Similarity	NPD6335	Approved
0.7737	Intermediate Similarity	NPD6616	Approved
0.7727	Intermediate Similarity	NPD6868	Approved
0.7687	Intermediate Similarity	NPD4522	Approved
0.7669	Intermediate Similarity	NPD6009	Approved
0.7647	Intermediate Similarity	NPD6370	Approved
0.7634	Intermediate Similarity	NPD8297	Approved
0.7612	Intermediate Similarity	NPD6314	Approved
0.7612	Intermediate Similarity	NPD6313	Approved
0.7574	Intermediate Similarity	NPD6015	Approved
0.7574	Intermediate Similarity	NPD6016	Approved
0.7557	Intermediate Similarity	NPD6650	Approved
0.7557	Intermediate Similarity	NPD6649	Approved
0.7537	Intermediate Similarity	NPD7115	Discovery
0.7518	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.7481	Intermediate Similarity	NPD4634	Approved
0.7462	Intermediate Similarity	NPD7320	Approved
0.7462	Intermediate Similarity	NPD6881	Approved
0.7462	Intermediate Similarity	NPD6899	Approved
0.7447	Intermediate Similarity	NPD7319	Approved
0.7429	Intermediate Similarity	NPD8293	Discontinued
0.7405	Intermediate Similarity	NPD6373	Approved
0.7405	Intermediate Similarity	NPD6372	Approved
0.7385	Intermediate Similarity	NPD5697	Approved
0.7368	Intermediate Similarity	NPD6882	Approved
0.7357	Intermediate Similarity	NPD7507	Approved
0.7348	Intermediate Similarity	NPD7290	Approved
0.7348	Intermediate Similarity	NPD6883	Approved
0.7348	Intermediate Similarity	NPD7102	Approved
0.7348	Intermediate Similarity	NPD5169	Approved
0.7328	Intermediate Similarity	NPD5168	Approved
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.7293	Intermediate Similarity	NPD6847	Approved
0.7293	Intermediate Similarity	NPD6869	Approved
0.7293	Intermediate Similarity	NPD6617	Approved
0.7293	Intermediate Similarity	NPD8130	Phase 1
0.7293	Intermediate Similarity	NPD5127	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7214	Intermediate Similarity	NPD7604	Phase 2
0.7209	Intermediate Similarity	NPD5211	Phase 2
0.7197	Intermediate Similarity	NPD6011	Approved
0.7121	Intermediate Similarity	NPD5701	Approved
0.7099	Intermediate Similarity	NPD5141	Approved
0.7092	Intermediate Similarity	NPD8328	Phase 3
0.7068	Intermediate Similarity	NPD5128	Approved
0.7068	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4696	Approved
0.7054	Intermediate Similarity	NPD5286	Approved
0.7054	Intermediate Similarity	NPD5285	Approved
0.7045	Intermediate Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD5225	Approved
0.6947	Remote Similarity	NPD5224	Approved
0.6947	Remote Similarity	NPD5226	Approved
0.6947	Remote Similarity	NPD4633	Approved
0.6912	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4755	Approved
0.6894	Remote Similarity	NPD5174	Approved
0.6894	Remote Similarity	NPD5175	Approved
0.687	Remote Similarity	NPD5223	Approved
0.6866	Remote Similarity	NPD6412	Phase 2
0.6857	Remote Similarity	NPD7327	Approved
0.6857	Remote Similarity	NPD7328	Approved
0.6835	Remote Similarity	NPD6274	Approved
0.6831	Remote Similarity	NPD8033	Approved
0.6831	Remote Similarity	NPD7503	Approved
0.6831	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4729	Approved
0.6815	Remote Similarity	NPD4730	Approved
0.6809	Remote Similarity	NPD7516	Approved
0.6794	Remote Similarity	NPD4700	Approved
0.6786	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6317	Approved
0.6769	Remote Similarity	NPD6084	Phase 2
0.6769	Remote Similarity	NPD6083	Phase 2
0.6761	Remote Similarity	NPD8377	Approved
0.6761	Remote Similarity	NPD8294	Approved
0.6741	Remote Similarity	NPD6614	Approved
0.6739	Remote Similarity	NPD6053	Discontinued
0.6715	Remote Similarity	NPD5251	Approved
0.6715	Remote Similarity	NPD5248	Approved
0.6715	Remote Similarity	NPD5249	Phase 3
0.6715	Remote Similarity	NPD5250	Approved
0.6715	Remote Similarity	NPD5247	Approved
0.6713	Remote Similarity	NPD8380	Approved
0.6713	Remote Similarity	NPD8335	Approved
0.6713	Remote Similarity	NPD8379	Approved
0.6713	Remote Similarity	NPD8296	Approved
0.6713	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6618	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD8515	Approved
0.6597	Remote Similarity	NPD8513	Phase 3
0.6597	Remote Similarity	NPD6909	Approved
0.6597	Remote Similarity	NPD6921	Approved
0.6597	Remote Similarity	NPD6908	Approved
0.6597	Remote Similarity	NPD8517	Approved
0.6597	Remote Similarity	NPD8516	Approved
0.6594	Remote Similarity	NPD6371	Approved
0.6591	Remote Similarity	NPD7638	Approved
0.6591	Remote Similarity	NPD4225	Approved
0.6591	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD6686	Approved
0.6567	Remote Similarity	NPD5091	Approved
0.6565	Remote Similarity	NPD5222	Approved
0.6565	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5221	Approved
0.6533	Remote Similarity	NPD7260	Phase 2
0.6519	Remote Similarity	NPD4754	Approved
0.6515	Remote Similarity	NPD5173	Approved
0.6512	Remote Similarity	NPD6079	Approved
0.6494	Remote Similarity	NPD6333	Approved
0.6494	Remote Similarity	NPD6334	Approved
0.6489	Remote Similarity	NPD5695	Phase 3
0.6489	Remote Similarity	NPD5210	Approved
0.6489	Remote Similarity	NPD4629	Approved
0.6475	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5135	Approved
0.6462	Remote Similarity	NPD6399	Phase 3
0.6461	Remote Similarity	NPD6784	Approved
0.6461	Remote Similarity	NPD6785	Approved
0.6439	Remote Similarity	NPD4697	Phase 3
0.6403	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7799	Discontinued
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5328	Approved
0.6357	Remote Similarity	NPD4753	Phase 2
0.6357	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD8133	Approved
0.6336	Remote Similarity	NPD4202	Approved
0.6308	Remote Similarity	NPD5785	Approved
0.6284	Remote Similarity	NPD6067	Discontinued
0.6279	Remote Similarity	NPD6903	Approved
0.6275	Remote Similarity	NPD6845	Suspended
0.6269	Remote Similarity	NPD7902	Approved
0.6267	Remote Similarity	NPD8074	Phase 3
0.6241	Remote Similarity	NPD5654	Approved
0.6231	Remote Similarity	NPD6904	Approved
0.6231	Remote Similarity	NPD6080	Approved
0.6231	Remote Similarity	NPD6673	Approved
0.6212	Remote Similarity	NPD5778	Approved
0.6212	Remote Similarity	NPD5779	Approved
0.6204	Remote Similarity	NPD7632	Discontinued
0.6202	Remote Similarity	NPD3573	Approved
0.6197	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7236	Approved
0.6194	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5363	Approved
0.6165	Remote Similarity	NPD7748	Approved
0.6165	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6148	Remote Similarity	NPD5959	Approved
0.6143	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7983	Approved
0.6136	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD5284	Approved
0.6136	Remote Similarity	NPD5693	Phase 1
0.6136	Remote Similarity	NPD7637	Suspended
0.6136	Remote Similarity	NPD5281	Approved
0.6136	Remote Similarity	NPD6411	Approved
0.6124	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7521	Approved
0.6124	Remote Similarity	NPD5330	Approved
0.6124	Remote Similarity	NPD5786	Approved
0.6124	Remote Similarity	NPD7146	Approved
0.6124	Remote Similarity	NPD7334	Approved
0.6124	Remote Similarity	NPD6409	Approved
0.6124	Remote Similarity	NPD3618	Phase 1
0.6124	Remote Similarity	NPD6684	Approved
0.6115	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD7239	Suspended
0.6047	Remote Similarity	NPD5329	Approved
0.6045	Remote Similarity	NPD6001	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