NPASS Compound

Structure

NPC473255 OpenBabel07101718322D 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 0.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 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 1 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 8 1 0 0 0 0 6 19 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 27 1 0 0 0 0 9 24 1 0 0 0 0 10 20 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 10 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 1 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:	1.819
LogD:	1.544
LogS:	-3.628
# Rotatable Bonds:	1
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.265
Synthetic Accessibility Score:	6.52
Fsp3:	0.857
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:	-5.356
MDCK Permeability:	2.896064324886538e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.326

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.823
Plasma Protein Binding (PPB):	46.32341003417969%
Volume Distribution (VD):	0.412
Pgp-substrate:	27.703968048095703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.688
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	2.382
Half-life (T1/2):	0.512

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.37
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.78
Skin Sensitization:	0.307
Carcinogencity:	0.786
Eye Corrosion:	0.004
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: NPC473255

Natural Product ID:	NPC473255
*Common Name:**	Anomanolide E
IUPAC Name:	(1R,4R,5R)-4-hydroxy-4,5-dimethyl-7-[(5S,6S,8S,9S,10R,13S,14S,16R,17S)-5,6,16,17-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 E
Standard InCHIKey:	XBHRORXHTAXVQY-NEUAYHDJSA-N
Standard InCHI:	InChI=1S/C28H40O8/c1-23-12-17(18(13-23)36-22(32)26(23,4)33)28(35)21(31)11-16-14-10-20(30)27(34)8-5-6-19(29)25(27,3)15(14)7-9-24(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]2C[C@H](O)[C@]2([C@]1(C)C(=O)C=CC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387868
PubChem CID:	44423057
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[494673]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[494673]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[494673]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[494673]
NPT27	Others	Unspecified		IC50	>	20.0	ug.mL-1	PMID[494673]

☑ 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 NPC473255 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	275
0.1-0.2	1550
0.2-0.3	5070
0.3-0.4	8755
0.4-0.5	11813
0.5-0.6	6453
0.6-0.7	5847
0.7-0.8	2593
0.8-0.85	261
0.85-0.9	75
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9658	High Similarity	NPC473265
0.9658	High Similarity	NPC470882
0.9496	High Similarity	NPC470880
0.9328	High Similarity	NPC473253
0.9224	High Similarity	NPC473203
0.9068	High Similarity	NPC470921
0.8862	High Similarity	NPC231529
0.8793	High Similarity	NPC194100
0.876	High Similarity	NPC473396
0.8739	High Similarity	NPC61520
0.8739	High Similarity	NPC469488
0.8729	High Similarity	NPC474654
0.8729	High Similarity	NPC287343
0.8729	High Similarity	NPC122033
0.8729	High Similarity	NPC470854
0.8729	High Similarity	NPC97908
0.872	High Similarity	NPC471855
0.8718	High Similarity	NPC243354
0.8707	High Similarity	NPC280782
0.8699	High Similarity	NPC305496
0.8678	High Similarity	NPC269642
0.8678	High Similarity	NPC222688
0.8667	High Similarity	NPC476961
0.8655	High Similarity	NPC297179
0.8655	High Similarity	NPC17772
0.8655	High Similarity	NPC329736
0.8644	High Similarity	NPC251236
0.8644	High Similarity	NPC96312
0.8644	High Similarity	NPC40632
0.8644	High Similarity	NPC328374
0.8632	High Similarity	NPC49451
0.8632	High Similarity	NPC208998
0.8632	High Similarity	NPC7921
0.8618	High Similarity	NPC174367
0.8618	High Similarity	NPC47113
0.8583	High Similarity	NPC470777
0.8571	High Similarity	NPC471854
0.856	High Similarity	NPC471407
0.8559	High Similarity	NPC473798
0.8548	High Similarity	NPC287423
0.8525	High Similarity	NPC65858
0.8522	High Similarity	NPC293850
0.8512	High Similarity	NPC109973
0.8512	High Similarity	NPC471406
0.85	High Similarity	NPC204552
0.85	High Similarity	NPC311554
0.85	High Similarity	NPC251310
0.85	High Similarity	NPC257457
0.85	High Similarity	NPC188667
0.8487	Intermediate Similarity	NPC270929
0.8487	Intermediate Similarity	NPC152199
0.8487	Intermediate Similarity	NPC207217
0.8487	Intermediate Similarity	NPC49492
0.8487	Intermediate Similarity	NPC266728
0.8487	Intermediate Similarity	NPC235539
0.8487	Intermediate Similarity	NPC134869
0.8487	Intermediate Similarity	NPC270958
0.848	Intermediate Similarity	NPC311534
0.848	Intermediate Similarity	NPC473620
0.8475	Intermediate Similarity	NPC52634
0.8475	Intermediate Similarity	NPC962
0.8475	Intermediate Similarity	NPC194273
0.8475	Intermediate Similarity	NPC250109
0.8475	Intermediate Similarity	NPC320118
0.8475	Intermediate Similarity	NPC198539
0.8468	Intermediate Similarity	NPC473635
0.8468	Intermediate Similarity	NPC293112
0.8462	Intermediate Similarity	NPC146945
0.8462	Intermediate Similarity	NPC472003
0.8462	Intermediate Similarity	NPC171888
0.8462	Intermediate Similarity	NPC471243
0.8455	Intermediate Similarity	NPC43252
0.8455	Intermediate Similarity	NPC11895
0.8455	Intermediate Similarity	NPC473979
0.8455	Intermediate Similarity	NPC469789
0.8455	Intermediate Similarity	NPC135038
0.8443	Intermediate Similarity	NPC46570
0.8443	Intermediate Similarity	NPC102822
0.8443	Intermediate Similarity	NPC477046
0.843	Intermediate Similarity	NPC475041
0.843	Intermediate Similarity	NPC319570
0.8425	Intermediate Similarity	NPC254614
0.8425	Intermediate Similarity	NPC100390
0.8417	Intermediate Similarity	NPC218970
0.8417	Intermediate Similarity	NPC470959
0.8417	Intermediate Similarity	NPC476965
0.8417	Intermediate Similarity	NPC239273
0.8403	Intermediate Similarity	NPC471398
0.8403	Intermediate Similarity	NPC18547
0.8403	Intermediate Similarity	NPC300051
0.8403	Intermediate Similarity	NPC474906
0.839	Intermediate Similarity	NPC474927
0.839	Intermediate Similarity	NPC11252
0.839	Intermediate Similarity	NPC289312
0.839	Intermediate Similarity	NPC71348
0.8387	Intermediate Similarity	NPC24651
0.8387	Intermediate Similarity	NPC470922
0.8387	Intermediate Similarity	NPC172154
0.8387	Intermediate Similarity	NPC8369
0.8387	Intermediate Similarity	NPC81736
0.8376	Intermediate Similarity	NPC197428
0.8376	Intermediate Similarity	NPC235077
0.8374	Intermediate Similarity	NPC107493
0.8374	Intermediate Similarity	NPC470265
0.8374	Intermediate Similarity	NPC23786
0.8374	Intermediate Similarity	NPC313528
0.8374	Intermediate Similarity	NPC170538
0.8361	Intermediate Similarity	NPC112038
0.8361	Intermediate Similarity	NPC472004
0.8361	Intermediate Similarity	NPC79579
0.8347	Intermediate Similarity	NPC473720
0.8347	Intermediate Similarity	NPC118638
0.8333	Intermediate Similarity	NPC16081
0.8333	Intermediate Similarity	NPC473888
0.8333	Intermediate Similarity	NPC173686
0.8319	Intermediate Similarity	NPC178981
0.8319	Intermediate Similarity	NPC202889
0.8319	Intermediate Similarity	NPC255017
0.8319	Intermediate Similarity	NPC471252
0.8306	Intermediate Similarity	NPC18945
0.8306	Intermediate Similarity	NPC267822
0.8306	Intermediate Similarity	NPC91693
0.8306	Intermediate Similarity	NPC105926
0.8306	Intermediate Similarity	NPC265557
0.8306	Intermediate Similarity	NPC67251
0.8306	Intermediate Similarity	NPC120724
0.8305	Intermediate Similarity	NPC201992
0.8305	Intermediate Similarity	NPC213320
0.8293	Intermediate Similarity	NPC67569
0.8291	Intermediate Similarity	NPC27814
0.8291	Intermediate Similarity	NPC41405
0.8291	Intermediate Similarity	NPC470257
0.8281	Intermediate Similarity	NPC34963
0.8279	Intermediate Similarity	NPC475775
0.8279	Intermediate Similarity	NPC476529
0.8279	Intermediate Similarity	NPC476960
0.8279	Intermediate Similarity	NPC5292
0.8276	Intermediate Similarity	NPC44063
0.8276	Intermediate Similarity	NPC144854
0.8276	Intermediate Similarity	NPC3316
0.8268	Intermediate Similarity	NPC476966
0.8268	Intermediate Similarity	NPC35109
0.8268	Intermediate Similarity	NPC221414
0.8264	Intermediate Similarity	NPC470171
0.8264	Intermediate Similarity	NPC470775
0.8264	Intermediate Similarity	NPC176513
0.8261	Intermediate Similarity	NPC29705
0.825	Intermediate Similarity	NPC268238
0.825	Intermediate Similarity	NPC178289
0.825	Intermediate Similarity	NPC45218
0.825	Intermediate Similarity	NPC326542
0.825	Intermediate Similarity	NPC473898
0.825	Intermediate Similarity	NPC323821
0.825	Intermediate Similarity	NPC143268
0.824	Intermediate Similarity	NPC475194
0.824	Intermediate Similarity	NPC476729
0.824	Intermediate Similarity	NPC169818
0.824	Intermediate Similarity	NPC8374
0.8235	Intermediate Similarity	NPC207251
0.8235	Intermediate Similarity	NPC473397
0.8235	Intermediate Similarity	NPC234042
0.8235	Intermediate Similarity	NPC152117
0.8235	Intermediate Similarity	NPC170487
0.8235	Intermediate Similarity	NPC90769
0.8235	Intermediate Similarity	NPC205534
0.8235	Intermediate Similarity	NPC474516
0.8226	Intermediate Similarity	NPC28532
0.8226	Intermediate Similarity	NPC312833
0.822	Intermediate Similarity	NPC320383
0.822	Intermediate Similarity	NPC6206
0.822	Intermediate Similarity	NPC471093
0.822	Intermediate Similarity	NPC474786
0.822	Intermediate Similarity	NPC5284
0.822	Intermediate Similarity	NPC137104
0.8217	Intermediate Similarity	NPC58029
0.8217	Intermediate Similarity	NPC469673
0.8211	Intermediate Similarity	NPC107338
0.8211	Intermediate Similarity	NPC109607
0.8211	Intermediate Similarity	NPC474585
0.8211	Intermediate Similarity	NPC474370
0.8205	Intermediate Similarity	NPC277017
0.8205	Intermediate Similarity	NPC273155
0.8205	Intermediate Similarity	NPC94529
0.8205	Intermediate Similarity	NPC154608
0.8205	Intermediate Similarity	NPC192813
0.8203	Intermediate Similarity	NPC220757
0.8203	Intermediate Similarity	NPC173347
0.8203	Intermediate Similarity	NPC196921
0.8203	Intermediate Similarity	NPC279478
0.8203	Intermediate Similarity	NPC241935
0.8197	Intermediate Similarity	NPC153440
0.8197	Intermediate Similarity	NPC470776
0.819	Intermediate Similarity	NPC96377
0.819	Intermediate Similarity	NPC196528
0.8189	Intermediate Similarity	NPC69273
0.8189	Intermediate Similarity	NPC168899
0.8189	Intermediate Similarity	NPC293623
0.8182	Intermediate Similarity	NPC298278
0.8182	Intermediate Similarity	NPC473233
0.8182	Intermediate Similarity	NPC88945

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 NPC473255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	1841
0.2-0.3	4014
0.3-0.4	1957
0.4-0.5	597
0.5-0.6	244
0.6-0.7	121
0.7-0.8	110
0.8-0.85	15
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8983	High Similarity	NPD6319	Approved
0.8699	High Similarity	NPD7078	Approved
0.8689	High Similarity	NPD7492	Approved
0.8667	High Similarity	NPD6054	Approved
0.8629	High Similarity	NPD7736	Approved
0.8618	High Similarity	NPD6616	Approved
0.8547	High Similarity	NPD8297	Approved
0.8525	High Similarity	NPD6370	Approved
0.8475	Intermediate Similarity	NPD4632	Approved
0.8462	Intermediate Similarity	NPD6650	Approved
0.8462	Intermediate Similarity	NPD6649	Approved
0.8443	Intermediate Similarity	NPD6015	Approved
0.8443	Intermediate Similarity	NPD6016	Approved
0.8376	Intermediate Similarity	NPD4634	Approved
0.8374	Intermediate Similarity	NPD5988	Approved
0.8362	Intermediate Similarity	NPD6899	Approved
0.8362	Intermediate Similarity	NPD6881	Approved
0.8362	Intermediate Similarity	NPD7320	Approved
0.8361	Intermediate Similarity	NPD6059	Approved
0.8291	Intermediate Similarity	NPD6372	Approved
0.8291	Intermediate Similarity	NPD6373	Approved
0.8276	Intermediate Similarity	NPD5697	Approved
0.8254	Intermediate Similarity	NPD8293	Discontinued
0.8235	Intermediate Similarity	NPD6882	Approved
0.822	Intermediate Similarity	NPD6883	Approved
0.822	Intermediate Similarity	NPD7290	Approved
0.822	Intermediate Similarity	NPD7102	Approved
0.819	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD6675	Approved
0.819	Intermediate Similarity	NPD5739	Approved
0.8151	Intermediate Similarity	NPD6847	Approved
0.8151	Intermediate Similarity	NPD6617	Approved
0.8151	Intermediate Similarity	NPD6869	Approved
0.8151	Intermediate Similarity	NPD8130	Phase 1
0.8136	Intermediate Similarity	NPD6012	Approved
0.8136	Intermediate Similarity	NPD6014	Approved
0.8136	Intermediate Similarity	NPD6013	Approved
0.8115	Intermediate Similarity	NPD6009	Approved
0.8051	Intermediate Similarity	NPD6011	Approved
0.8016	Intermediate Similarity	NPD7604	Phase 2
0.8	Intermediate Similarity	NPD5983	Phase 2
0.7984	Intermediate Similarity	NPD7319	Approved
0.7967	Intermediate Similarity	NPD7115	Discovery
0.7966	Intermediate Similarity	NPD5701	Approved
0.7913	Intermediate Similarity	NPD5286	Approved
0.7913	Intermediate Similarity	NPD4696	Approved
0.7913	Intermediate Similarity	NPD5285	Approved
0.7899	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6336	Discontinued
0.7891	Intermediate Similarity	NPD7507	Approved
0.7881	Intermediate Similarity	NPD6008	Approved
0.7874	Intermediate Similarity	NPD8328	Phase 3
0.7778	Intermediate Similarity	NPD5224	Approved
0.7778	Intermediate Similarity	NPD5211	Phase 2
0.7778	Intermediate Similarity	NPD5225	Approved
0.7778	Intermediate Similarity	NPD5226	Approved
0.7778	Intermediate Similarity	NPD4633	Approved
0.7769	Intermediate Similarity	NPD6033	Approved
0.7739	Intermediate Similarity	NPD4755	Approved
0.7712	Intermediate Similarity	NPD5175	Approved
0.7712	Intermediate Similarity	NPD5174	Approved
0.7705	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7101	Approved
0.7698	Intermediate Similarity	NPD7100	Approved
0.7692	Intermediate Similarity	NPD5223	Approved
0.7667	Intermediate Similarity	NPD6412	Phase 2
0.7647	Intermediate Similarity	NPD5141	Approved
0.7619	Intermediate Similarity	NPD6335	Approved
0.7607	Intermediate Similarity	NPD4700	Approved
0.7603	Intermediate Similarity	NPD4730	Approved
0.7603	Intermediate Similarity	NPD4729	Approved
0.76	Intermediate Similarity	NPD6274	Approved
0.7586	Intermediate Similarity	NPD6084	Phase 2
0.7586	Intermediate Similarity	NPD6083	Phase 2
0.7578	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6317	Approved
0.754	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5248	Approved
0.748	Intermediate Similarity	NPD5250	Approved
0.748	Intermediate Similarity	NPD6313	Approved
0.748	Intermediate Similarity	NPD6314	Approved
0.748	Intermediate Similarity	NPD5251	Approved
0.748	Intermediate Similarity	NPD5247	Approved
0.748	Intermediate Similarity	NPD5249	Phase 3
0.7438	Intermediate Similarity	NPD4768	Approved
0.7438	Intermediate Similarity	NPD4767	Approved
0.7422	Intermediate Similarity	NPD7516	Approved
0.7373	Intermediate Similarity	NPD5696	Approved
0.735	Intermediate Similarity	NPD5221	Approved
0.735	Intermediate Similarity	NPD5222	Approved
0.735	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7327	Approved
0.7344	Intermediate Similarity	NPD7328	Approved
0.7317	Intermediate Similarity	NPD5128	Approved
0.7308	Intermediate Similarity	NPD6921	Approved
0.7308	Intermediate Similarity	NPD6908	Approved
0.7308	Intermediate Similarity	NPD6909	Approved
0.7308	Intermediate Similarity	NPD7503	Approved
0.7308	Intermediate Similarity	NPD8033	Approved
0.7304	Intermediate Similarity	NPD6079	Approved
0.7288	Intermediate Similarity	NPD5173	Approved
0.728	Intermediate Similarity	NPD5215	Approved
0.728	Intermediate Similarity	NPD5216	Approved
0.728	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD4754	Approved
0.7265	Intermediate Similarity	NPD5210	Approved
0.7265	Intermediate Similarity	NPD4629	Approved
0.7265	Intermediate Similarity	NPD5695	Phase 3
0.7259	Intermediate Similarity	NPD5956	Approved
0.7258	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6399	Phase 3
0.7231	Intermediate Similarity	NPD8377	Approved
0.7231	Intermediate Similarity	NPD8294	Approved
0.7222	Intermediate Similarity	NPD6053	Discontinued
0.7203	Intermediate Similarity	NPD4697	Phase 3
0.72	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5169	Approved
0.72	Intermediate Similarity	NPD5135	Approved
0.7188	Intermediate Similarity	NPD6868	Approved
0.7176	Intermediate Similarity	NPD8379	Approved
0.7176	Intermediate Similarity	NPD8296	Approved
0.7176	Intermediate Similarity	NPD8378	Approved
0.7176	Intermediate Similarity	NPD8380	Approved
0.7176	Intermediate Similarity	NPD8335	Approved
0.7154	Intermediate Similarity	NPD4522	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD6334	Approved
0.7143	Intermediate Similarity	NPD6333	Approved
0.713	Intermediate Similarity	NPD4753	Phase 2
0.713	Intermediate Similarity	NPD5328	Approved
0.7119	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD7638	Approved
0.7043	Intermediate Similarity	NPD6903	Approved
0.704	Intermediate Similarity	NPD6686	Approved
0.7025	Intermediate Similarity	NPD7640	Approved
0.7025	Intermediate Similarity	NPD7639	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.6984	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6904	Approved
0.6983	Remote Similarity	NPD6080	Approved
0.6983	Remote Similarity	NPD6673	Approved
0.6977	Remote Similarity	NPD5167	Approved
0.6957	Remote Similarity	NPD7260	Phase 2
0.6957	Remote Similarity	NPD3573	Approved
0.6942	Remote Similarity	NPD4225	Approved
0.694	Remote Similarity	NPD6067	Discontinued
0.6929	Remote Similarity	NPD6371	Approved
0.6929	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8515	Approved
0.6917	Remote Similarity	NPD8517	Approved
0.6917	Remote Similarity	NPD8516	Approved
0.6917	Remote Similarity	NPD8513	Phase 3
0.6899	Remote Similarity	NPD8133	Approved
0.6897	Remote Similarity	NPD6672	Approved
0.6897	Remote Similarity	NPD5737	Approved
0.6897	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7748	Approved
0.6891	Remote Similarity	NPD5282	Discontinued
0.687	Remote Similarity	NPD5330	Approved
0.687	Remote Similarity	NPD7521	Approved
0.687	Remote Similarity	NPD6409	Approved
0.687	Remote Similarity	NPD3618	Phase 1
0.687	Remote Similarity	NPD7334	Approved
0.687	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7146	Approved
0.687	Remote Similarity	NPD6684	Approved
0.6864	Remote Similarity	NPD6411	Approved
0.6864	Remote Similarity	NPD7515	Phase 2
0.6864	Remote Similarity	NPD5281	Approved
0.6864	Remote Similarity	NPD5284	Approved
0.6829	Remote Similarity	NPD1700	Approved
0.68	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5329	Approved
0.6772	Remote Similarity	NPD5168	Approved
0.675	Remote Similarity	NPD7900	Approved
0.675	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6001	Approved
0.6728	Remote Similarity	NPD7799	Discontinued
0.6724	Remote Similarity	NPD5690	Phase 2
0.6724	Remote Similarity	NPD6098	Approved
0.6723	Remote Similarity	NPD8034	Phase 2
0.6723	Remote Similarity	NPD6050	Approved
0.6723	Remote Similarity	NPD5693	Phase 1
0.6723	Remote Similarity	NPD5694	Approved
0.6723	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD3665	Phase 1
0.6696	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD4786	Approved
0.6696	Remote Similarity	NPD3666	Approved
0.6695	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6101	Approved
0.6693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6845	Suspended
0.6639	Remote Similarity	NPD5785	Approved
0.6639	Remote Similarity	NPD5207	Approved
0.6639	Remote Similarity	NPD5692	Phase 3

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