NPASS Compound

Structure

NPC473265 OpenBabel07101718292D 36 41 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 -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 -0.8660 -0.5000 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 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 0.0000 -0.0000 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 0.8660 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 0.0000 -1.0000 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 -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 10 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 7 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 25 1 6 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 13 1 1 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 27 1 6 0 0 0 20 30 1 0 0 0 0 21 28 1 1 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 22 36 1 0 0 0 0 23 26 1 1 0 0 0 24 28 1 1 0 0 0 25 27 1 6 0 0 0 26 4 1 1 0 0 0 26 33 1 0 0 0 0 27 34 1 6 0 0 0 28 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.27
Volume:	503.918
LogP:	1.827
LogD:	2.032
LogS:	-3.919
# Rotatable Bonds:	1
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	6.277
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269
MDCK Permeability:	8.706367225386202e-06
Pgp-inhibitor:	0.185
Pgp-substrate:	0.072
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.848
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	59.05677032470703%
Volume Distribution (VD):	0.515
Pgp-substrate:	19.684221267700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.785
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.669
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	3.292
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.237
Carcinogencity:	0.377
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC473265

Natural Product ID:	NPC473265
*Common Name:**	Anomanolide F
IUPAC Name:	(1R,4R,5R)-4-hydroxy-4,5-dimethyl-7-[(4S,5R,8S,9S,10R,13S,14S,16R,17S)-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]-2-oxabicyclo[3.2.1]octan-3-one
Synonyms:	Anomanolide F
Standard InCHIKey:	IIXRXLFGAXOZNE-VOWCFRKOSA-N
Standard InCHI:	InChI=1S/C28H40O8/c1-23-12-17(18(13-23)36-22(32)26(23,4)33)28(35)21(31)11-16-14-7-10-27(34)20(30)6-5-19(29)25(27,3)15(14)8-9-24(16,28)2/h5-6,14-18,20-21,30-31,33-35H,7-13H2,1-4H3/t14-,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]2CC[C@]2([C@]1(C)C(=O)C=C[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388494
PubChem CID:	44423064
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	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.	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[475439]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475439]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475439]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475439]
NPT27	Others	Unspecified		IC50	>	20.0	ug.mL-1	PMID[475439]

☑ 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 NPC473265 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	272
0.1-0.2	1472
0.2-0.3	4588
0.3-0.4	8141
0.4-0.5	12130
0.5-0.6	6901
0.6-0.7	6149
0.7-0.8	2679
0.8-0.85	301
0.85-0.9	58
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC470880
0.9829	High Similarity	NPC470882
0.9661	High Similarity	NPC473253
0.9658	High Similarity	NPC473255
0.9068	High Similarity	NPC61520
0.9068	High Similarity	NPC473203
0.9062	High Similarity	NPC473396
0.8983	High Similarity	NPC329736
0.8917	High Similarity	NPC470921
0.8871	High Similarity	NPC231529
0.8843	High Similarity	NPC269642
0.8843	High Similarity	NPC222688
0.8814	High Similarity	NPC270929
0.877	High Similarity	NPC469789
0.876	High Similarity	NPC46570
0.8739	High Similarity	NPC471854
0.873	High Similarity	NPC471855
0.871	High Similarity	NPC287423
0.8699	High Similarity	NPC8369
0.8689	High Similarity	NPC107493
0.8689	High Similarity	NPC470265
0.8689	High Similarity	NPC23786
0.8678	High Similarity	NPC109973
0.8667	High Similarity	NPC251310
0.8655	High Similarity	NPC266728
0.8655	High Similarity	NPC49492
0.8644	High Similarity	NPC194100
0.8644	High Similarity	NPC962
0.8644	High Similarity	NPC250109
0.864	High Similarity	NPC473888
0.864	High Similarity	NPC311534
0.864	High Similarity	NPC473620
0.8629	High Similarity	NPC293112
0.8607	High Similarity	NPC67569
0.8595	High Similarity	NPC475041
0.8583	High Similarity	NPC239273
0.8571	High Similarity	NPC471407
0.856	High Similarity	NPC305496
0.8548	High Similarity	NPC172154
0.8548	High Similarity	NPC81736
0.8548	High Similarity	NPC470922
0.8548	High Similarity	NPC8374
0.8525	High Similarity	NPC474370
0.8525	High Similarity	NPC79579
0.8525	High Similarity	NPC476961
0.8516	High Similarity	NPC469673
0.8512	High Similarity	NPC311554
0.8512	High Similarity	NPC257457
0.8512	High Similarity	NPC473720
0.8504	High Similarity	NPC196921
0.8504	High Similarity	NPC220757
0.85	High Similarity	NPC148458
0.848	Intermediate Similarity	NPC47113
0.848	Intermediate Similarity	NPC473635
0.848	Intermediate Similarity	NPC174367
0.8473	Intermediate Similarity	NPC473233
0.8468	Intermediate Similarity	NPC11895
0.8468	Intermediate Similarity	NPC473979
0.8468	Intermediate Similarity	NPC120724
0.8468	Intermediate Similarity	NPC67251
0.845	Intermediate Similarity	NPC471234
0.845	Intermediate Similarity	NPC476823
0.8443	Intermediate Similarity	NPC469488
0.8443	Intermediate Similarity	NPC5292
0.8443	Intermediate Similarity	NPC472933
0.8443	Intermediate Similarity	NPC264954
0.8438	Intermediate Similarity	NPC34963
0.843	Intermediate Similarity	NPC474654
0.843	Intermediate Similarity	NPC176513
0.843	Intermediate Similarity	NPC470854
0.843	Intermediate Similarity	NPC470775
0.843	Intermediate Similarity	NPC287343
0.843	Intermediate Similarity	NPC97908
0.843	Intermediate Similarity	NPC218970
0.843	Intermediate Similarity	NPC122033
0.8425	Intermediate Similarity	NPC35109
0.8425	Intermediate Similarity	NPC221414
0.8417	Intermediate Similarity	NPC243354
0.8417	Intermediate Similarity	NPC326542
0.8403	Intermediate Similarity	NPC280782
0.8403	Intermediate Similarity	NPC207251
0.84	Intermediate Similarity	NPC476729
0.84	Intermediate Similarity	NPC24651
0.8387	Intermediate Similarity	NPC28532
0.8387	Intermediate Similarity	NPC88326
0.8387	Intermediate Similarity	NPC170538
0.8387	Intermediate Similarity	NPC153700
0.8374	Intermediate Similarity	NPC472004
0.8374	Intermediate Similarity	NPC474585
0.8374	Intermediate Similarity	NPC476962
0.8374	Intermediate Similarity	NPC112038
0.8372	Intermediate Similarity	NPC469674
0.8372	Intermediate Similarity	NPC58029
0.8361	Intermediate Similarity	NPC709
0.8361	Intermediate Similarity	NPC50774
0.8361	Intermediate Similarity	NPC17772
0.8361	Intermediate Similarity	NPC153440
0.8361	Intermediate Similarity	NPC297179
0.8361	Intermediate Similarity	NPC470776
0.8359	Intermediate Similarity	NPC279478
0.8359	Intermediate Similarity	NPC241935
0.8359	Intermediate Similarity	NPC173347
0.8347	Intermediate Similarity	NPC40632
0.8347	Intermediate Similarity	NPC474734
0.8347	Intermediate Similarity	NPC190286
0.8347	Intermediate Similarity	NPC96312
0.8347	Intermediate Similarity	NPC270958
0.8347	Intermediate Similarity	NPC328374
0.8347	Intermediate Similarity	NPC251236
0.8333	Intermediate Similarity	NPC7921
0.8333	Intermediate Similarity	NPC208998
0.8333	Intermediate Similarity	NPC472926
0.8333	Intermediate Similarity	NPC317210
0.8333	Intermediate Similarity	NPC52634
0.8333	Intermediate Similarity	NPC108721
0.8333	Intermediate Similarity	NPC73300
0.8333	Intermediate Similarity	NPC49451
0.832	Intermediate Similarity	NPC204812
0.832	Intermediate Similarity	NPC265557
0.832	Intermediate Similarity	NPC18945
0.832	Intermediate Similarity	NPC91693
0.832	Intermediate Similarity	NPC105926
0.8319	Intermediate Similarity	NPC472003
0.8306	Intermediate Similarity	NPC472001
0.8306	Intermediate Similarity	NPC472000
0.8306	Intermediate Similarity	NPC471999
0.8306	Intermediate Similarity	NPC202051
0.8305	Intermediate Similarity	NPC214644
0.8295	Intermediate Similarity	NPC102316
0.8295	Intermediate Similarity	NPC231240
0.8293	Intermediate Similarity	NPC476960
0.8293	Intermediate Similarity	NPC476529
0.8293	Intermediate Similarity	NPC470777
0.8293	Intermediate Similarity	NPC475775
0.8293	Intermediate Similarity	NPC319570
0.8293	Intermediate Similarity	NPC475520
0.8281	Intermediate Similarity	NPC473593
0.8281	Intermediate Similarity	NPC476966
0.8279	Intermediate Similarity	NPC470171
0.8279	Intermediate Similarity	NPC167606
0.8279	Intermediate Similarity	NPC140055
0.8279	Intermediate Similarity	NPC470959
0.8279	Intermediate Similarity	NPC470492
0.8279	Intermediate Similarity	NPC20302
0.8279	Intermediate Similarity	NPC472927
0.8279	Intermediate Similarity	NPC472934
0.8279	Intermediate Similarity	NPC476965
0.8279	Intermediate Similarity	NPC286528
0.8268	Intermediate Similarity	NPC152091
0.8268	Intermediate Similarity	NPC117702
0.8268	Intermediate Similarity	NPC469757
0.8268	Intermediate Similarity	NPC471357
0.8268	Intermediate Similarity	NPC146456
0.8264	Intermediate Similarity	NPC178289
0.8264	Intermediate Similarity	NPC473798
0.8264	Intermediate Similarity	NPC471398
0.8264	Intermediate Similarity	NPC147912
0.8264	Intermediate Similarity	NPC67259
0.8264	Intermediate Similarity	NPC300051
0.8254	Intermediate Similarity	NPC32868
0.8254	Intermediate Similarity	NPC241456
0.825	Intermediate Similarity	NPC71348
0.825	Intermediate Similarity	NPC100267
0.825	Intermediate Similarity	NPC269530
0.825	Intermediate Similarity	NPC475524
0.824	Intermediate Similarity	NPC313528
0.824	Intermediate Similarity	NPC65858
0.824	Intermediate Similarity	NPC312833
0.8235	Intermediate Similarity	NPC197428
0.8235	Intermediate Similarity	NPC235077
0.8231	Intermediate Similarity	NPC316915
0.8226	Intermediate Similarity	NPC471406
0.8226	Intermediate Similarity	NPC107338
0.8226	Intermediate Similarity	NPC109607
0.822	Intermediate Similarity	NPC293850
0.8217	Intermediate Similarity	NPC213634
0.8211	Intermediate Similarity	NPC188667
0.8211	Intermediate Similarity	NPC118638
0.8211	Intermediate Similarity	NPC204552
0.8211	Intermediate Similarity	NPC21326
0.8209	Intermediate Similarity	NPC25887
0.8203	Intermediate Similarity	NPC245094
0.8197	Intermediate Similarity	NPC474046
0.8197	Intermediate Similarity	NPC235539
0.8197	Intermediate Similarity	NPC134869
0.8197	Intermediate Similarity	NPC259306
0.8197	Intermediate Similarity	NPC207217
0.8197	Intermediate Similarity	NPC176840
0.8197	Intermediate Similarity	NPC152199
0.8197	Intermediate Similarity	NPC470628
0.8189	Intermediate Similarity	NPC15095
0.8182	Intermediate Similarity	NPC202889
0.8182	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC51978
0.8182	Intermediate Similarity	NPC25909
0.8182	Intermediate Similarity	NPC178981
0.8182	Intermediate Similarity	NPC194273
0.8182	Intermediate Similarity	NPC320118
0.8182	Intermediate Similarity	NPC198539
0.8175	Intermediate Similarity	NPC135038

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 NPC473265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1693
0.2-0.3	3902
0.3-0.4	2139
0.4-0.5	650
0.5-0.6	264
0.6-0.7	137
0.7-0.8	106
0.8-0.85	13
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8833	High Similarity	NPD6319	Approved
0.856	High Similarity	NPD7078	Approved
0.8548	High Similarity	NPD7492	Approved
0.8525	High Similarity	NPD6054	Approved
0.8492	Intermediate Similarity	NPD7736	Approved
0.848	Intermediate Similarity	NPD6616	Approved
0.8403	Intermediate Similarity	NPD8297	Approved
0.8387	Intermediate Similarity	NPD6370	Approved
0.8333	Intermediate Similarity	NPD4632	Approved
0.8319	Intermediate Similarity	NPD6650	Approved
0.8319	Intermediate Similarity	NPD6649	Approved
0.8306	Intermediate Similarity	NPD6016	Approved
0.8306	Intermediate Similarity	NPD6015	Approved
0.8279	Intermediate Similarity	NPD7115	Discovery
0.824	Intermediate Similarity	NPD5988	Approved
0.8235	Intermediate Similarity	NPD4634	Approved
0.8226	Intermediate Similarity	NPD6059	Approved
0.822	Intermediate Similarity	NPD6899	Approved
0.822	Intermediate Similarity	NPD6881	Approved
0.822	Intermediate Similarity	NPD7320	Approved
0.8151	Intermediate Similarity	NPD6373	Approved
0.8151	Intermediate Similarity	NPD6372	Approved
0.814	Intermediate Similarity	NPD7319	Approved
0.8136	Intermediate Similarity	NPD5697	Approved
0.8125	Intermediate Similarity	NPD8293	Discontinued
0.8099	Intermediate Similarity	NPD6882	Approved
0.8083	Intermediate Similarity	NPD6883	Approved
0.8083	Intermediate Similarity	NPD7290	Approved
0.8083	Intermediate Similarity	NPD7102	Approved
0.8051	Intermediate Similarity	NPD6675	Approved
0.8051	Intermediate Similarity	NPD6402	Approved
0.8051	Intermediate Similarity	NPD5739	Approved
0.8051	Intermediate Similarity	NPD7128	Approved
0.8047	Intermediate Similarity	NPD7507	Approved
0.8017	Intermediate Similarity	NPD6847	Approved
0.8017	Intermediate Similarity	NPD6617	Approved
0.8017	Intermediate Similarity	NPD6869	Approved
0.8017	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7984	Intermediate Similarity	NPD6009	Approved
0.7949	Intermediate Similarity	NPD5211	Phase 2
0.7917	Intermediate Similarity	NPD6011	Approved
0.7891	Intermediate Similarity	NPD7604	Phase 2
0.7874	Intermediate Similarity	NPD5983	Phase 2
0.7833	Intermediate Similarity	NPD5701	Approved
0.7815	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD5285	Approved
0.7778	Intermediate Similarity	NPD5286	Approved
0.7778	Intermediate Similarity	NPD4696	Approved
0.7769	Intermediate Similarity	NPD6336	Discontinued
0.7769	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD8328	Phase 3
0.775	Intermediate Similarity	NPD6008	Approved
0.7652	Intermediate Similarity	NPD6033	Approved
0.7647	Intermediate Similarity	NPD4633	Approved
0.7647	Intermediate Similarity	NPD5226	Approved
0.7647	Intermediate Similarity	NPD5224	Approved
0.7647	Intermediate Similarity	NPD5225	Approved
0.7607	Intermediate Similarity	NPD4755	Approved
0.7583	Intermediate Similarity	NPD5175	Approved
0.7583	Intermediate Similarity	NPD5174	Approved
0.7581	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7100	Approved
0.7578	Intermediate Similarity	NPD7101	Approved
0.7563	Intermediate Similarity	NPD5223	Approved
0.7541	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.748	Intermediate Similarity	NPD4730	Approved
0.748	Intermediate Similarity	NPD4729	Approved
0.748	Intermediate Similarity	NPD6274	Approved
0.7479	Intermediate Similarity	NPD4700	Approved
0.7462	Intermediate Similarity	NPD8033	Approved
0.7462	Intermediate Similarity	NPD7503	Approved
0.7462	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6083	Phase 2
0.7458	Intermediate Similarity	NPD6084	Phase 2
0.7442	Intermediate Similarity	NPD7516	Approved
0.7422	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6317	Approved
0.7385	Intermediate Similarity	NPD8377	Approved
0.7385	Intermediate Similarity	NPD8294	Approved
0.7381	Intermediate Similarity	NPD6053	Discontinued
0.7364	Intermediate Similarity	NPD6313	Approved
0.7364	Intermediate Similarity	NPD6314	Approved
0.736	Intermediate Similarity	NPD5247	Approved
0.736	Intermediate Similarity	NPD5248	Approved
0.736	Intermediate Similarity	NPD5249	Phase 3
0.736	Intermediate Similarity	NPD5251	Approved
0.736	Intermediate Similarity	NPD5250	Approved
0.7333	Intermediate Similarity	NPD7640	Approved
0.7333	Intermediate Similarity	NPD7639	Approved
0.7328	Intermediate Similarity	NPD8379	Approved
0.7328	Intermediate Similarity	NPD8296	Approved
0.7328	Intermediate Similarity	NPD8378	Approved
0.7328	Intermediate Similarity	NPD8380	Approved
0.7328	Intermediate Similarity	NPD8335	Approved
0.7317	Intermediate Similarity	NPD4768	Approved
0.7317	Intermediate Similarity	NPD4767	Approved
0.7258	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5696	Approved
0.725	Intermediate Similarity	NPD7638	Approved
0.725	Intermediate Similarity	NPD4225	Approved
0.7227	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD5221	Approved
0.7227	Intermediate Similarity	NPD5222	Approved
0.7222	Intermediate Similarity	NPD6371	Approved
0.72	Intermediate Similarity	NPD5128	Approved
0.72	Intermediate Similarity	NPD6686	Approved
0.7197	Intermediate Similarity	NPD8513	Phase 3
0.7197	Intermediate Similarity	NPD6908	Approved
0.7197	Intermediate Similarity	NPD8515	Approved
0.7197	Intermediate Similarity	NPD6909	Approved
0.7197	Intermediate Similarity	NPD6921	Approved
0.7197	Intermediate Similarity	NPD8517	Approved
0.7197	Intermediate Similarity	NPD8516	Approved
0.7179	Intermediate Similarity	NPD6079	Approved
0.7167	Intermediate Similarity	NPD5173	Approved
0.7165	Intermediate Similarity	NPD5215	Approved
0.7165	Intermediate Similarity	NPD5216	Approved
0.7165	Intermediate Similarity	NPD5217	Approved
0.7154	Intermediate Similarity	NPD4754	Approved
0.7153	Intermediate Similarity	NPD5956	Approved
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7119	Intermediate Similarity	NPD6399	Phase 3
0.7101	Intermediate Similarity	NPD7260	Phase 2
0.7087	Intermediate Similarity	NPD5135	Approved
0.7087	Intermediate Similarity	NPD5169	Approved
0.7087	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4697	Phase 3
0.7077	Intermediate Similarity	NPD6868	Approved
0.7045	Intermediate Similarity	NPD4522	Approved
0.7042	Intermediate Similarity	NPD6334	Approved
0.7042	Intermediate Similarity	NPD6333	Approved
0.7031	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD4753	Phase 2
0.7009	Intermediate Similarity	NPD5328	Approved
0.7008	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4202	Approved
0.6953	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6885	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD5167	Approved
0.6864	Remote Similarity	NPD6673	Approved
0.6864	Remote Similarity	NPD6904	Approved
0.6864	Remote Similarity	NPD6080	Approved
0.6852	Remote Similarity	NPD7799	Discontinued
0.6838	Remote Similarity	NPD6067	Discontinued
0.6838	Remote Similarity	NPD3573	Approved
0.6833	Remote Similarity	NPD5779	Approved
0.6833	Remote Similarity	NPD5778	Approved
0.6812	Remote Similarity	NPD8074	Phase 3
0.681	Remote Similarity	NPD5363	Approved
0.6809	Remote Similarity	NPD6845	Suspended
0.68	Remote Similarity	NPD7632	Discontinued
0.678	Remote Similarity	NPD5737	Approved
0.678	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6672	Approved
0.6777	Remote Similarity	NPD7748	Approved
0.6777	Remote Similarity	NPD5282	Discontinued
0.6769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7521	Approved
0.6752	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6684	Approved
0.6752	Remote Similarity	NPD7146	Approved
0.6752	Remote Similarity	NPD7334	Approved
0.6752	Remote Similarity	NPD6409	Approved
0.6752	Remote Similarity	NPD3618	Phase 1
0.6752	Remote Similarity	NPD5786	Approved
0.6752	Remote Similarity	NPD5330	Approved
0.675	Remote Similarity	NPD7983	Approved
0.675	Remote Similarity	NPD5693	Phase 1
0.675	Remote Similarity	NPD7637	Suspended
0.675	Remote Similarity	NPD7515	Phase 2
0.675	Remote Similarity	NPD5284	Approved
0.675	Remote Similarity	NPD5281	Approved
0.675	Remote Similarity	NPD6411	Approved
0.6719	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7236	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6639	Remote Similarity	NPD6001	Approved
0.6639	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5694	Approved
0.6612	Remote Similarity	NPD8034	Phase 2
0.6612	Remote Similarity	NPD6050	Approved
0.6612	Remote Similarity	NPD8035	Phase 2
0.661	Remote Similarity	NPD6098	Approved
0.661	Remote Similarity	NPD5690	Phase 2

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