NPASS Compound

Structure

NPC474858 OpenBabel07101718292D 36 39 0 0 1 0 0 0 0 0999 V2000 -3.4432 4.2681 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 -1.0000 0.0000 C 0 0 0 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 -7.2132 1.1812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6200 2.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2187 1.0767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0322 2.9037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6309 1.8857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4499 3.6082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6301 3.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 3.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 4.8208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0377 2.7992 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 -1.9487 3.2976 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8731 4.2082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7796 4.9067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4554 3.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 4.1636 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0486 2.5902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 -3.8676 4.3127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 26 1 0 0 0 0 12 19 2 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 25 2 0 0 0 0 14 18 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 20 29 1 0 0 0 0 21 35 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 36 1 1 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 33 1 0 0 0 0 26 30 2 0 0 0 0 26 36 1 0 0 0 0 27 31 2 0 0 0 0 27 35 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	495.23
Volume:	507.418
LogP:	3.513
LogD:	3.671
LogS:	-4.269
# Rotatable Bonds:	11
TPSA:	83.53
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	4.426
Fsp3:	0.429
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:	-4.654
MDCK Permeability:	3.7393398088170215e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	56.926002502441406%
Volume Distribution (VD):	0.724
Pgp-substrate:	17.743595123291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.904

ADMET: Excretion

Clearance (CL):	11.476
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.938
Human Hepatotoxicity (H-HT):	0.643
Drug-inuced Liver Injury (DILI):	0.74
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.942
Carcinogencity:	0.161
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC474858

Natural Product ID:	NPC474858
*Common Name:**	Pervilleine F
IUPAC Name:	[(3S,6S)-8-methyl-3-(2-phenylacetyl)oxy-8-azabicyclo[3.2.1]octan-6-yl] (E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoate
Synonyms:	Pervilleine F
Standard InCHIKey:	FKUUUFHXKIFGSF-BFKYYIPTSA-N
Standard InCHI:	InChI=1S/C28H33NO7/c1-29-20-15-21(35-27(31)14-18-8-6-5-7-9-18)17-22(29)23(16-20)36-26(30)11-10-19-12-24(32-2)28(34-4)25(13-19)33-3/h5-13,20-23H,14-17H2,1-4H3/b11-10+/t20?,21-,22?,23-/m0/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@H]2CC3N(C2C[C@H](C3)OC(=O)Cc2ccccc2)C)cc(c1OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485486
PubChem CID:	44576224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids 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
NPO33258	erythroxylum pervillei	Species	Erythroxylaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754602]

☑ 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
ED50	8

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570876]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[570876]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570876]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570876]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[570876]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[570876]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[570876]

☑ 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 NPC474858 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	248
0.1-0.2	1136
0.2-0.3	3515
0.3-0.4	10425
0.4-0.5	7941
0.5-0.6	7146
0.6-0.7	11371
0.7-0.8	901
0.8-0.85	1
0.85-0.9	1
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC329992
0.9503	High Similarity	NPC329816
0.9419	High Similarity	NPC329640
0.9268	High Similarity	NPC473562
0.9125	High Similarity	NPC329717
0.9114	High Similarity	NPC26353
0.8706	High Similarity	NPC475566
0.8485	Intermediate Similarity	NPC35345
0.8242	Intermediate Similarity	NPC202771
0.8242	Intermediate Similarity	NPC2173
0.8242	Intermediate Similarity	NPC328700
0.8242	Intermediate Similarity	NPC119818
0.8136	Intermediate Similarity	NPC141440
0.8092	Intermediate Similarity	NPC35680
0.8084	Intermediate Similarity	NPC158900
0.8061	Intermediate Similarity	NPC169742
0.8022	Intermediate Similarity	NPC73020
0.8022	Intermediate Similarity	NPC124302
0.8022	Intermediate Similarity	NPC70290
0.8022	Intermediate Similarity	NPC14622
0.8022	Intermediate Similarity	NPC46744
0.8022	Intermediate Similarity	NPC215098
0.8022	Intermediate Similarity	NPC83019
0.7967	Intermediate Similarity	NPC204580
0.7935	Intermediate Similarity	NPC226652
0.7935	Intermediate Similarity	NPC72788
0.7935	Intermediate Similarity	NPC314100
0.7935	Intermediate Similarity	NPC120671
0.7914	Intermediate Similarity	NPC214239
0.7898	Intermediate Similarity	NPC211386
0.7826	Intermediate Similarity	NPC46180
0.7802	Intermediate Similarity	NPC94499
0.7785	Intermediate Similarity	NPC72796
0.7785	Intermediate Similarity	NPC44245
0.7784	Intermediate Similarity	NPC476434
0.7778	Intermediate Similarity	NPC162694
0.7758	Intermediate Similarity	NPC182119
0.7754	Intermediate Similarity	NPC286135
0.7744	Intermediate Similarity	NPC213482
0.7701	Intermediate Similarity	NPC473748
0.7692	Intermediate Similarity	NPC79184
0.7692	Intermediate Similarity	NPC307042
0.7683	Intermediate Similarity	NPC474158
0.7677	Intermediate Similarity	NPC210674
0.7665	Intermediate Similarity	NPC473091
0.7658	Intermediate Similarity	NPC288743
0.7647	Intermediate Similarity	NPC222185
0.763	Intermediate Similarity	NPC180306
0.763	Intermediate Similarity	NPC319749
0.7624	Intermediate Similarity	NPC18306
0.7622	Intermediate Similarity	NPC470646
0.7622	Intermediate Similarity	NPC469978
0.7622	Intermediate Similarity	NPC475000
0.7614	Intermediate Similarity	NPC227683
0.761	Intermediate Similarity	NPC145769
0.7607	Intermediate Similarity	NPC176586
0.7607	Intermediate Similarity	NPC210354
0.7602	Intermediate Similarity	NPC477380
0.7602	Intermediate Similarity	NPC301897
0.758	Intermediate Similarity	NPC476399
0.7576	Intermediate Similarity	NPC293201
0.7574	Intermediate Similarity	NPC75695
0.7572	Intermediate Similarity	NPC218614
0.7562	Intermediate Similarity	NPC224941
0.7562	Intermediate Similarity	NPC311430
0.7561	Intermediate Similarity	NPC106920
0.7561	Intermediate Similarity	NPC273657
0.7561	Intermediate Similarity	NPC28326
0.7558	Intermediate Similarity	NPC477885
0.7558	Intermediate Similarity	NPC472860
0.7557	Intermediate Similarity	NPC474708
0.7554	Intermediate Similarity	NPC63152
0.7545	Intermediate Similarity	NPC40654
0.7545	Intermediate Similarity	NPC102934
0.7545	Intermediate Similarity	NPC262804
0.7545	Intermediate Similarity	NPC252402
0.7544	Intermediate Similarity	NPC471746
0.7542	Intermediate Similarity	NPC309692
0.7541	Intermediate Similarity	NPC469437
0.7541	Intermediate Similarity	NPC208890
0.7539	Intermediate Similarity	NPC80472
0.7532	Intermediate Similarity	NPC118419
0.753	Intermediate Similarity	NPC287275
0.753	Intermediate Similarity	NPC193779
0.7529	Intermediate Similarity	NPC258322
0.7529	Intermediate Similarity	NPC146277
0.7529	Intermediate Similarity	NPC19380
0.7529	Intermediate Similarity	NPC191352
0.7529	Intermediate Similarity	NPC474656
0.7527	Intermediate Similarity	NPC33256
0.7516	Intermediate Similarity	NPC288238
0.7516	Intermediate Similarity	NPC225745
0.7516	Intermediate Similarity	NPC143895
0.7516	Intermediate Similarity	NPC113236
0.7516	Intermediate Similarity	NPC214036
0.7516	Intermediate Similarity	NPC209229
0.7515	Intermediate Similarity	NPC191158
0.7515	Intermediate Similarity	NPC270811
0.7515	Intermediate Similarity	NPC471073
0.7515	Intermediate Similarity	NPC243891
0.7515	Intermediate Similarity	NPC177644
0.7515	Intermediate Similarity	NPC62354
0.75	Intermediate Similarity	NPC98809
0.75	Intermediate Similarity	NPC194841
0.75	Intermediate Similarity	NPC155063
0.75	Intermediate Similarity	NPC40237
0.75	Intermediate Similarity	NPC476342
0.75	Intermediate Similarity	NPC476394
0.75	Intermediate Similarity	NPC11147
0.75	Intermediate Similarity	NPC477884
0.75	Intermediate Similarity	NPC475845
0.75	Intermediate Similarity	NPC151423
0.75	Intermediate Similarity	NPC309744
0.7486	Intermediate Similarity	NPC230098
0.7486	Intermediate Similarity	NPC241704
0.7486	Intermediate Similarity	NPC474470
0.7486	Intermediate Similarity	NPC280778
0.7485	Intermediate Similarity	NPC178195
0.7485	Intermediate Similarity	NPC153620
0.7485	Intermediate Similarity	NPC348849
0.7485	Intermediate Similarity	NPC24257
0.7485	Intermediate Similarity	NPC186507
0.7471	Intermediate Similarity	NPC163883
0.7471	Intermediate Similarity	NPC95498
0.7471	Intermediate Similarity	NPC93498
0.7471	Intermediate Similarity	NPC246566
0.7471	Intermediate Similarity	NPC476373
0.7471	Intermediate Similarity	NPC267091
0.7471	Intermediate Similarity	NPC477164
0.7471	Intermediate Similarity	NPC473732
0.7471	Intermediate Similarity	NPC239966
0.7471	Intermediate Similarity	NPC203020
0.7471	Intermediate Similarity	NPC151425
0.7471	Intermediate Similarity	NPC53889
0.747	Intermediate Similarity	NPC27106
0.747	Intermediate Similarity	NPC113089
0.7468	Intermediate Similarity	NPC299010
0.7458	Intermediate Similarity	NPC118162
0.7458	Intermediate Similarity	NPC320471
0.7458	Intermediate Similarity	NPC83049
0.7458	Intermediate Similarity	NPC75958
0.7457	Intermediate Similarity	NPC226759
0.7457	Intermediate Similarity	NPC108456
0.7456	Intermediate Similarity	NPC316989
0.7456	Intermediate Similarity	NPC474648
0.7455	Intermediate Similarity	NPC470811
0.7455	Intermediate Similarity	NPC477697
0.7455	Intermediate Similarity	NPC474966
0.7455	Intermediate Similarity	NPC185607
0.7455	Intermediate Similarity	NPC474288
0.7455	Intermediate Similarity	NPC477696
0.7455	Intermediate Similarity	NPC244338
0.7448	Intermediate Similarity	NPC476500
0.7443	Intermediate Similarity	NPC57812
0.7443	Intermediate Similarity	NPC474324
0.7443	Intermediate Similarity	NPC252960
0.7442	Intermediate Similarity	NPC145425
0.744	Intermediate Similarity	NPC139839
0.744	Intermediate Similarity	NPC469539
0.744	Intermediate Similarity	NPC117463
0.744	Intermediate Similarity	NPC327352
0.744	Intermediate Similarity	NPC477375
0.744	Intermediate Similarity	NPC470511
0.744	Intermediate Similarity	NPC198129
0.744	Intermediate Similarity	NPC252281
0.744	Intermediate Similarity	NPC470088
0.744	Intermediate Similarity	NPC469540
0.7436	Intermediate Similarity	NPC127604
0.7436	Intermediate Similarity	NPC112571
0.7436	Intermediate Similarity	NPC186845
0.7436	Intermediate Similarity	NPC88297
0.7436	Intermediate Similarity	NPC9891
0.7436	Intermediate Similarity	NPC50683
0.7436	Intermediate Similarity	NPC285725
0.7429	Intermediate Similarity	NPC34376
0.7427	Intermediate Similarity	NPC40033
0.7427	Intermediate Similarity	NPC68882
0.7427	Intermediate Similarity	NPC44730
0.7427	Intermediate Similarity	NPC477377
0.7427	Intermediate Similarity	NPC144162
0.7427	Intermediate Similarity	NPC475116
0.7425	Intermediate Similarity	NPC471590
0.7425	Intermediate Similarity	NPC136278
0.7425	Intermediate Similarity	NPC296575
0.7423	Intermediate Similarity	NPC470962
0.7423	Intermediate Similarity	NPC44573
0.7414	Intermediate Similarity	NPC289811
0.7414	Intermediate Similarity	NPC87317
0.7414	Intermediate Similarity	NPC325122
0.7414	Intermediate Similarity	NPC160780
0.7412	Intermediate Similarity	NPC32079
0.7412	Intermediate Similarity	NPC13985
0.7412	Intermediate Similarity	NPC210642
0.741	Intermediate Similarity	NPC70853
0.741	Intermediate Similarity	NPC218841
0.741	Intermediate Similarity	NPC9966
0.741	Intermediate Similarity	NPC92693
0.741	Intermediate Similarity	NPC110337
0.741	Intermediate Similarity	NPC473090
0.741	Intermediate Similarity	NPC18211

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 NPC474858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	554
0.2-0.3	1084
0.3-0.4	2195
0.4-0.5	2506
0.5-0.6	1641
0.6-0.7	886
0.7-0.8	112
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD5353	Approved
0.8562	High Similarity	NPD6386	Approved
0.8562	High Similarity	NPD6385	Approved
0.8494	Intermediate Similarity	NPD5242	Approved
0.8242	Intermediate Similarity	NPD5005	Approved
0.8242	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD5006	Approved
0.8101	Intermediate Similarity	NPD4236	Phase 3
0.8101	Intermediate Similarity	NPD4237	Approved
0.8022	Intermediate Similarity	NPD4420	Approved
0.7888	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7038	Approved
0.7841	Intermediate Similarity	NPD7039	Approved
0.7791	Intermediate Similarity	NPD5297	Approved
0.7778	Intermediate Similarity	NPD5677	Discontinued
0.7771	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3146	Approved
0.7744	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7549	Discontinued
0.7679	Intermediate Similarity	NPD6873	Phase 2
0.7676	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4210	Discontinued
0.759	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7466	Approved
0.7485	Intermediate Similarity	NPD5772	Approved
0.7485	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5773	Approved
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5688	Approved
0.7453	Intermediate Similarity	NPD5689	Approved
0.7442	Intermediate Similarity	NPD5978	Approved
0.7442	Intermediate Similarity	NPD5977	Approved
0.7439	Intermediate Similarity	NPD2654	Approved
0.7429	Intermediate Similarity	NPD6107	Approved
0.7418	Intermediate Similarity	NPD6851	Approved
0.7418	Intermediate Similarity	NPD6853	Approved
0.741	Intermediate Similarity	NPD7124	Phase 2
0.7407	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4481	Phase 3
0.7386	Intermediate Similarity	NPD5710	Approved
0.7386	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5494	Approved
0.7368	Intermediate Similarity	NPD5890	Approved
0.7368	Intermediate Similarity	NPD7110	Phase 1
0.7368	Intermediate Similarity	NPD5889	Approved
0.7368	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6032	Approved
0.7358	Intermediate Similarity	NPD5718	Phase 2
0.7353	Intermediate Similarity	NPD3455	Phase 2
0.7342	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7329	Intermediate Similarity	NPD4622	Approved
0.7329	Intermediate Similarity	NPD4618	Approved
0.7326	Intermediate Similarity	NPD6844	Discontinued
0.7321	Intermediate Similarity	NPD7447	Phase 1
0.7318	Intermediate Similarity	NPD2163	Approved
0.7316	Intermediate Similarity	NPD7565	Approved
0.7312	Intermediate Similarity	NPD3531	Approved
0.7312	Intermediate Similarity	NPD3530	Approved
0.7312	Intermediate Similarity	NPD3532	Approved
0.7312	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4678	Approved
0.731	Intermediate Similarity	NPD4675	Approved
0.7302	Intermediate Similarity	NPD2973	Approved
0.7302	Intermediate Similarity	NPD2975	Approved
0.7302	Intermediate Similarity	NPD2974	Approved
0.7299	Intermediate Similarity	NPD6788	Approved
0.7299	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3687	Approved
0.7294	Intermediate Similarity	NPD3686	Approved
0.7284	Intermediate Similarity	NPD2492	Phase 1
0.7278	Intermediate Similarity	NPD5312	Approved
0.7278	Intermediate Similarity	NPD5313	Approved
0.7278	Intermediate Similarity	NPD8156	Discontinued
0.7273	Intermediate Similarity	NPD2897	Discontinued
0.7267	Intermediate Similarity	NPD3142	Approved
0.7267	Intermediate Similarity	NPD6677	Suspended
0.7267	Intermediate Similarity	NPD3140	Approved
0.7262	Intermediate Similarity	NPD7213	Phase 3
0.7262	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7212	Phase 2
0.7257	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2240	Approved
0.7256	Intermediate Similarity	NPD2239	Approved
0.7254	Intermediate Similarity	NPD7497	Discontinued
0.7249	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6111	Discontinued
0.7239	Intermediate Similarity	NPD2200	Suspended
0.7235	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1934	Approved
0.7225	Intermediate Similarity	NPD37	Approved
0.7225	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8099	Discontinued
0.7222	Intermediate Similarity	NPD8252	Approved
0.7222	Intermediate Similarity	NPD8251	Approved
0.7209	Intermediate Similarity	NPD6585	Discontinued
0.72	Intermediate Similarity	NPD4966	Approved
0.72	Intermediate Similarity	NPD4965	Approved
0.72	Intermediate Similarity	NPD4967	Phase 2
0.7198	Intermediate Similarity	NPD6297	Approved
0.7195	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4580	Approved
0.7188	Intermediate Similarity	NPD4107	Approved
0.7184	Intermediate Similarity	NPD2977	Approved
0.7184	Intermediate Similarity	NPD2978	Approved
0.7182	Intermediate Similarity	NPD5844	Phase 1
0.7179	Intermediate Similarity	NPD7999	Approved
0.7177	Intermediate Similarity	NPD6625	Approved
0.7175	Intermediate Similarity	NPD6746	Phase 2
0.7174	Intermediate Similarity	NPD2971	Approved
0.7174	Intermediate Similarity	NPD2968	Approved
0.7169	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4357	Discontinued
0.715	Intermediate Similarity	NPD2493	Approved
0.715	Intermediate Similarity	NPD2494	Approved
0.7143	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5241	Discontinued
0.7135	Intermediate Similarity	NPD3640	Phase 3
0.7135	Intermediate Similarity	NPD3639	Approved
0.7135	Intermediate Similarity	NPD3641	Approved
0.7128	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3383	Approved
0.7126	Intermediate Similarity	NPD5177	Phase 3
0.7126	Intermediate Similarity	NPD3384	Approved
0.7126	Intermediate Similarity	NPD4162	Approved
0.7126	Intermediate Similarity	NPD3060	Approved
0.7126	Intermediate Similarity	NPD3382	Approved
0.7125	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6234	Discontinued
0.7112	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3882	Suspended
0.709	Intermediate Similarity	NPD7296	Approved
0.7086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2575	Approved
0.7081	Intermediate Similarity	NPD7281	Phase 3
0.7081	Intermediate Similarity	NPD7280	Phase 3
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3450	Approved
0.7062	Intermediate Similarity	NPD3452	Approved
0.7062	Intermediate Similarity	NPD4482	Phase 3
0.7062	Intermediate Similarity	NPD6971	Discontinued
0.7059	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4005	Discontinued
0.7052	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7827	Phase 1
0.7048	Intermediate Similarity	NPD3454	Phase 3
0.7047	Intermediate Similarity	NPD8285	Discontinued
0.7041	Intermediate Similarity	NPD4583	Approved
0.7041	Intermediate Similarity	NPD4582	Approved
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7228	Approved
0.7033	Intermediate Similarity	NPD3818	Discontinued
0.703	Intermediate Similarity	NPD2567	Approved
0.703	Intermediate Similarity	NPD2569	Approved
0.703	Intermediate Similarity	NPD7047	Phase 3
0.7022	Intermediate Similarity	NPD6315	Phase 2
0.7022	Intermediate Similarity	NPD919	Approved
0.7021	Intermediate Similarity	NPD7291	Discontinued
0.7021	Intermediate Similarity	NPD7906	Approved
0.7018	Intermediate Similarity	NPD4123	Phase 3
0.7018	Intermediate Similarity	NPD3536	Discontinued
0.7018	Intermediate Similarity	NPD1424	Approved
0.7018	Intermediate Similarity	NPD4584	Approved
0.7011	Intermediate Similarity	NPD6875	Approved
0.7011	Intermediate Similarity	NPD6876	Approved
0.701	Intermediate Similarity	NPD5457	Discontinued
0.7006	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7608	Discontinued
0.7	Intermediate Similarity	NPD6808	Phase 2
0.7	Intermediate Similarity	NPD6666	Approved
0.7	Intermediate Similarity	NPD6667	Approved
0.6995	Remote Similarity	NPD7054	Approved
0.699	Remote Similarity	NPD6997	Phase 2
0.699	Remote Similarity	NPD4002	Approved
0.699	Remote Similarity	NPD4004	Approved
0.6989	Remote Similarity	NPD4585	Approved
0.6989	Remote Similarity	NPD7819	Suspended
0.6989	Remote Similarity	NPD2801	Approved
0.6984	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD5667	Approved
0.6981	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7930	Approved
0.6979	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5582	Discontinued

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