NPASS Compound

Structure

NPC471934 OpenBabel07101718282D 39 41 0 0 1 0 0 0 0 0999 V2000 1.5731 7.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3210 -0.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 4.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2870 -1.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 5.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9828 1.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8910 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1712 2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3716 1.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 6.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3429 -0.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0249 3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9779 -1.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 5.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 5.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6738 0.2107 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0249 2.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3052 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6471 -0.2710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 4.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3052 1.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4392 0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5731 1.2071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6416 -0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 2.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0483 0.5380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5731 2.2071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6956 0.0027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 3.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1416 -1.2416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3866 -0.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1589 1.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 3.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0265 0.7459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 2.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 8 19 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 31 1 0 0 0 0 15 36 1 0 0 0 0 17 6 1 1 0 0 0 17 29 1 0 0 0 0 18 7 1 1 0 0 0 18 30 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 32 2 0 0 0 0 21 37 1 0 0 0 0 22 19 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 23 20 1 1 0 0 0 23 24 1 0 0 0 0 24 28 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 26 28 1 0 0 0 0 26 37 1 1 0 0 0 27 38 1 6 0 0 0 28 39 1 1 0 0 0 29 34 2 0 0 0 0 29 38 1 0 0 0 0 30 35 2 0 0 0 0 30 39 1 0 0 0 0 31 9 1 6 0 0 0 31 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.3
Volume:	570.929
LogP:	4.021
LogD:	2.908
LogS:	-4.056
# Rotatable Bonds:	13
TPSA:	108.5
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.126
Synthetic Accessibility Score:	5.459
Fsp3:	0.677
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:	-4.796
MDCK Permeability:	5.360297654988244e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	83.944091796875%
Volume Distribution (VD):	2.218
Pgp-substrate:	10.173046112060547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.67
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.546

ADMET: Excretion

Clearance (CL):	6.162
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.954
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.583
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.322
Carcinogencity:	0.066
Eye Corrosion:	0.012
Eye Irritation:	0.016
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC471934

Natural Product ID:	NPC471934
*Common Name:**	(1R,2S,5Z,6R,7S,8R,9S,11S,2''s,2'''e,2''''s)-11,12-Epoxy-2,8-Di(2''-Methylbutanoyloxy)-9-(3'''-Methyl-2'''-Pentenoyloxy)-10(14)-Oplopen-3-One
IUPAC Name:	[(1Z,3S,3aR,5S,6R,7S,7aR)-1-ethylidene-3,6-bis[[(2S)-2-methylbutanoyl]oxy]-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-3,3a,5,6,7,7a-hexahydroinden-5-yl] (E)-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	WAQPPOMZPIGXAQ-SZJORUNGSA-N
Standard InCHI:	InChI=1S/C31H44O8/c1-10-16(5)14-21(32)37-26-19(8)22-23(20(13-4)25(33)27(22)38-29(34)17(6)11-2)24(31(9)15-36-31)28(26)39-30(35)18(7)12-3/h13-14,17-18,22-24,26-28H,8,10-12,15H2,1-7,9H3/b16-14+,20-13-/t17-,18-,22-,23+,24-,26-,27-,28+,31+/m0/s1
SMILES:	CCC(C)C(=O)OC1C(C2C(C(C(=O)C2=CC)OC(=O)C(C)CC)C(=C)C1OC(=O)C=C(C)CC)C3(CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298991
PubChem CID:	90683361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO27190	Pittocaulon filare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24842703]
NPO27190	Pittocaulon filare	Species	Asteraceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.55	umol	PMID[506844]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	11.07	%	PMID[506844]

☑ 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 NPC471934 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	264
0.1-0.2	1534
0.2-0.3	4789
0.3-0.4	8027
0.4-0.5	13948
0.5-0.6	7766
0.6-0.7	4989
0.7-0.8	1308
0.8-0.85	57
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9519	High Similarity	NPC471933
0.9126	High Similarity	NPC103088
0.9126	High Similarity	NPC470979
0.9126	High Similarity	NPC470975
0.88	High Similarity	NPC470974
0.88	High Similarity	NPC470978
0.8696	High Similarity	NPC470973
0.8679	High Similarity	NPC474716
0.8544	High Similarity	NPC471932
0.8496	Intermediate Similarity	NPC472667
0.8421	Intermediate Similarity	NPC4548
0.8411	Intermediate Similarity	NPC470980
0.8393	Intermediate Similarity	NPC470793
0.8364	Intermediate Similarity	NPC475495
0.835	Intermediate Similarity	NPC118159
0.8348	Intermediate Similarity	NPC310511
0.8333	Intermediate Similarity	NPC469558
0.8302	Intermediate Similarity	NPC470972
0.8288	Intermediate Similarity	NPC477093
0.8288	Intermediate Similarity	NPC475277
0.8288	Intermediate Similarity	NPC473522
0.8286	Intermediate Similarity	NPC469551
0.8273	Intermediate Similarity	NPC253906
0.8261	Intermediate Similarity	NPC143755
0.8205	Intermediate Similarity	NPC473802
0.8165	Intermediate Similarity	NPC475510
0.8165	Intermediate Similarity	NPC470192
0.8165	Intermediate Similarity	NPC475587
0.8148	Intermediate Similarity	NPC477127
0.8142	Intermediate Similarity	NPC178289
0.8136	Intermediate Similarity	NPC473919
0.8136	Intermediate Similarity	NPC473709
0.8131	Intermediate Similarity	NPC475750
0.8103	Intermediate Similarity	NPC145182
0.8103	Intermediate Similarity	NPC471126
0.8103	Intermediate Similarity	NPC471128
0.8103	Intermediate Similarity	NPC157252
0.8091	Intermediate Similarity	NPC473595
0.8091	Intermediate Similarity	NPC473939
0.8087	Intermediate Similarity	NPC470420
0.807	Intermediate Similarity	NPC477509
0.8067	Intermediate Similarity	NPC471939
0.8053	Intermediate Similarity	NPC470120
0.8051	Intermediate Similarity	NPC472399
0.8039	Intermediate Similarity	NPC475748
0.8036	Intermediate Similarity	NPC194619
0.8034	Intermediate Similarity	NPC52839
0.8018	Intermediate Similarity	NPC469370
0.8017	Intermediate Similarity	NPC5292
0.8017	Intermediate Similarity	NPC475520
0.8017	Intermediate Similarity	NPC175186
0.8	Intermediate Similarity	NPC180744
0.8	Intermediate Similarity	NPC471940
0.8	Intermediate Similarity	NPC475305
0.7982	Intermediate Similarity	NPC90472
0.7966	Intermediate Similarity	NPC257017
0.7966	Intermediate Similarity	NPC162009
0.7965	Intermediate Similarity	NPC475391
0.7963	Intermediate Similarity	NPC471757
0.7963	Intermediate Similarity	NPC105725
0.7963	Intermediate Similarity	NPC78127
0.7961	Intermediate Similarity	NPC221282
0.7951	Intermediate Similarity	NPC471170
0.7949	Intermediate Similarity	NPC107338
0.7949	Intermediate Similarity	NPC109607
0.7949	Intermediate Similarity	NPC472004
0.7946	Intermediate Similarity	NPC281624
0.7946	Intermediate Similarity	NPC473843
0.7946	Intermediate Similarity	NPC473594
0.7946	Intermediate Similarity	NPC474586
0.7946	Intermediate Similarity	NPC473975
0.7931	Intermediate Similarity	NPC257457
0.7931	Intermediate Similarity	NPC471125
0.7931	Intermediate Similarity	NPC171905
0.7931	Intermediate Similarity	NPC153440
0.7931	Intermediate Similarity	NPC475401
0.7931	Intermediate Similarity	NPC311554
0.7931	Intermediate Similarity	NPC159928
0.7931	Intermediate Similarity	NPC472397
0.7931	Intermediate Similarity	NPC473720
0.7931	Intermediate Similarity	NPC472758
0.7917	Intermediate Similarity	NPC473635
0.7913	Intermediate Similarity	NPC190286
0.7913	Intermediate Similarity	NPC476711
0.7913	Intermediate Similarity	NPC476710
0.7903	Intermediate Similarity	NPC471234
0.7899	Intermediate Similarity	NPC120724
0.7895	Intermediate Similarity	NPC159333
0.7895	Intermediate Similarity	NPC477126
0.7895	Intermediate Similarity	NPC474937
0.789	Intermediate Similarity	NPC19239
0.789	Intermediate Similarity	NPC474166
0.7886	Intermediate Similarity	NPC471855
0.7881	Intermediate Similarity	NPC472401
0.7881	Intermediate Similarity	NPC204731
0.7876	Intermediate Similarity	NPC174471
0.7876	Intermediate Similarity	NPC474871
0.7876	Intermediate Similarity	NPC260786
0.7876	Intermediate Similarity	NPC96739
0.787	Intermediate Similarity	NPC264477
0.787	Intermediate Similarity	NPC477511
0.7869	Intermediate Similarity	NPC104382
0.7869	Intermediate Similarity	NPC470851
0.7863	Intermediate Similarity	NPC19028
0.7863	Intermediate Similarity	NPC275696
0.7863	Intermediate Similarity	NPC22628
0.7863	Intermediate Similarity	NPC5989
0.7863	Intermediate Similarity	NPC255081
0.7863	Intermediate Similarity	NPC9674
0.7863	Intermediate Similarity	NPC475775
0.7863	Intermediate Similarity	NPC477092
0.7863	Intermediate Similarity	NPC471108
0.7863	Intermediate Similarity	NPC476529
0.7863	Intermediate Similarity	NPC5991
0.7863	Intermediate Similarity	NPC475041
0.7857	Intermediate Similarity	NPC273433
0.7851	Intermediate Similarity	NPC287423
0.785	Intermediate Similarity	NPC264378
0.7845	Intermediate Similarity	NPC476713
0.7845	Intermediate Similarity	NPC476712
0.7838	Intermediate Similarity	NPC471601
0.7833	Intermediate Similarity	NPC470922
0.7833	Intermediate Similarity	NPC145238
0.7833	Intermediate Similarity	NPC81736
0.7833	Intermediate Similarity	NPC172154
0.783	Intermediate Similarity	NPC17585
0.7826	Intermediate Similarity	NPC474872
0.7818	Intermediate Similarity	NPC169843
0.7815	Intermediate Similarity	NPC19464
0.7815	Intermediate Similarity	NPC222688
0.7815	Intermediate Similarity	NPC170538
0.7815	Intermediate Similarity	NPC269642
0.7807	Intermediate Similarity	NPC170212
0.7807	Intermediate Similarity	NPC221511
0.7807	Intermediate Similarity	NPC17138
0.7807	Intermediate Similarity	NPC101825
0.7807	Intermediate Similarity	NPC215643
0.7807	Intermediate Similarity	NPC151216
0.7807	Intermediate Similarity	NPC89227
0.7807	Intermediate Similarity	NPC265499
0.7807	Intermediate Similarity	NPC317687
0.7807	Intermediate Similarity	NPC473877
0.7805	Intermediate Similarity	NPC473838
0.7805	Intermediate Similarity	NPC475389
0.7798	Intermediate Similarity	NPC49393
0.7797	Intermediate Similarity	NPC474585
0.7797	Intermediate Similarity	NPC79579
0.7788	Intermediate Similarity	NPC20713
0.7788	Intermediate Similarity	NPC472215
0.7788	Intermediate Similarity	NPC472214
0.7787	Intermediate Similarity	NPC236999
0.7778	Intermediate Similarity	NPC118638
0.7769	Intermediate Similarity	NPC293112
0.7768	Intermediate Similarity	NPC470269
0.7759	Intermediate Similarity	NPC471127
0.7759	Intermediate Similarity	NPC234858
0.7759	Intermediate Similarity	NPC270478
0.7759	Intermediate Similarity	NPC270958
0.7759	Intermediate Similarity	NPC154363
0.7759	Intermediate Similarity	NPC148458
0.775	Intermediate Similarity	NPC473979
0.775	Intermediate Similarity	NPC11895
0.775	Intermediate Similarity	NPC469789
0.7748	Intermediate Similarity	NPC475571
0.7745	Intermediate Similarity	NPC231889
0.7742	Intermediate Similarity	NPC475139
0.7742	Intermediate Similarity	NPC180902
0.7739	Intermediate Similarity	NPC250109
0.7739	Intermediate Similarity	NPC202889
0.7739	Intermediate Similarity	NPC71889
0.7739	Intermediate Similarity	NPC33360
0.7739	Intermediate Similarity	NPC317210
0.7739	Intermediate Similarity	NPC962
0.7739	Intermediate Similarity	NPC194100
0.7731	Intermediate Similarity	NPC46570
0.7724	Intermediate Similarity	NPC231529
0.7724	Intermediate Similarity	NPC471407
0.7724	Intermediate Similarity	NPC470880
0.7724	Intermediate Similarity	NPC472770
0.7719	Intermediate Similarity	NPC317107
0.7719	Intermediate Similarity	NPC469656
0.7719	Intermediate Similarity	NPC474846
0.7719	Intermediate Similarity	NPC469655
0.7712	Intermediate Similarity	NPC469380
0.7712	Intermediate Similarity	NPC305260
0.7712	Intermediate Similarity	NPC270850
0.7706	Intermediate Similarity	NPC471767
0.7706	Intermediate Similarity	NPC476270
0.7705	Intermediate Similarity	NPC42399
0.7705	Intermediate Similarity	NPC473253
0.7705	Intermediate Similarity	NPC470882
0.7699	Intermediate Similarity	NPC474242
0.7692	Intermediate Similarity	NPC471854
0.7692	Intermediate Similarity	NPC329857
0.7692	Intermediate Similarity	NPC156252
0.7692	Intermediate Similarity	NPC239273
0.7692	Intermediate Similarity	NPC473590
0.7692	Intermediate Similarity	NPC10721
0.7692	Intermediate Similarity	NPC296822
0.7692	Intermediate Similarity	NPC469718

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 NPC471934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1947
0.2-0.3	3789
0.3-0.4	2071
0.4-0.5	700
0.5-0.6	212
0.6-0.7	157
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7807	Intermediate Similarity	NPD8297	Approved
0.7748	Intermediate Similarity	NPD6008	Approved
0.7647	Intermediate Similarity	NPD6319	Approved
0.7611	Intermediate Similarity	NPD6899	Approved
0.7611	Intermediate Similarity	NPD6881	Approved
0.7589	Intermediate Similarity	NPD6675	Approved
0.7589	Intermediate Similarity	NPD6402	Approved
0.7589	Intermediate Similarity	NPD7128	Approved
0.7589	Intermediate Similarity	NPD5739	Approved
0.7565	Intermediate Similarity	NPD6649	Approved
0.7565	Intermediate Similarity	NPD6650	Approved
0.7544	Intermediate Similarity	NPD6372	Approved
0.7544	Intermediate Similarity	NPD6373	Approved
0.7522	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7478	Intermediate Similarity	NPD7290	Approved
0.7478	Intermediate Similarity	NPD7102	Approved
0.7478	Intermediate Similarity	NPD6883	Approved
0.7459	Intermediate Similarity	NPD7604	Phase 2
0.7456	Intermediate Similarity	NPD7320	Approved
0.7455	Intermediate Similarity	NPD6648	Approved
0.7436	Intermediate Similarity	NPD4632	Approved
0.7414	Intermediate Similarity	NPD8130	Phase 1
0.7414	Intermediate Similarity	NPD6869	Approved
0.7414	Intermediate Similarity	NPD6847	Approved
0.7414	Intermediate Similarity	NPD6617	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7395	Intermediate Similarity	NPD6009	Approved
0.7391	Intermediate Similarity	NPD6012	Approved
0.7391	Intermediate Similarity	NPD6013	Approved
0.7391	Intermediate Similarity	NPD6014	Approved
0.7387	Intermediate Similarity	NPD5344	Discontinued
0.7368	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5701	Approved
0.7358	Intermediate Similarity	NPD46	Approved
0.7358	Intermediate Similarity	NPD6698	Approved
0.7355	Intermediate Similarity	NPD6054	Approved
0.7339	Intermediate Similarity	NPD6616	Approved
0.7339	Intermediate Similarity	NPD7507	Approved
0.7304	Intermediate Similarity	NPD6011	Approved
0.7295	Intermediate Similarity	NPD5983	Phase 2
0.728	Intermediate Similarity	NPD7078	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.7236	Intermediate Similarity	NPD6370	Approved
0.7222	Intermediate Similarity	NPD7736	Approved
0.7213	Intermediate Similarity	NPD6059	Approved
0.7212	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7638	Approved
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.72	Intermediate Similarity	NPD6336	Discontinued
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7319	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7639	Approved
0.713	Intermediate Similarity	NPD5693	Phase 1
0.7119	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1695	Approved
0.7097	Intermediate Similarity	NPD5988	Approved
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6371	Approved
0.7025	Intermediate Similarity	NPD6274	Approved
0.7018	Intermediate Similarity	NPD5211	Phase 2
0.7009	Intermediate Similarity	NPD6686	Approved
0.6992	Remote Similarity	NPD7101	Approved
0.6992	Remote Similarity	NPD7100	Approved
0.6991	Remote Similarity	NPD5285	Approved
0.6991	Remote Similarity	NPD5286	Approved
0.6991	Remote Similarity	NPD4696	Approved
0.6964	Remote Similarity	NPD4755	Approved
0.6964	Remote Similarity	NPD6083	Phase 2
0.6964	Remote Similarity	NPD6084	Phase 2
0.6944	Remote Similarity	NPD6673	Approved
0.6944	Remote Similarity	NPD6080	Approved
0.6944	Remote Similarity	NPD6904	Approved
0.6937	Remote Similarity	NPD5695	Phase 3
0.6911	Remote Similarity	NPD6335	Approved
0.6897	Remote Similarity	NPD5141	Approved
0.6891	Remote Similarity	NPD4634	Approved
0.6881	Remote Similarity	NPD7838	Discovery
0.687	Remote Similarity	NPD5224	Approved
0.687	Remote Similarity	NPD5225	Approved
0.687	Remote Similarity	NPD5226	Approved
0.687	Remote Similarity	NPD4633	Approved
0.6864	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7516	Approved
0.6852	Remote Similarity	NPD5737	Approved
0.6852	Remote Similarity	NPD6672	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6829	Remote Similarity	NPD6317	Approved
0.6822	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD7521	Approved
0.6822	Remote Similarity	NPD6409	Approved
0.6822	Remote Similarity	NPD7334	Approved
0.6822	Remote Similarity	NPD7146	Approved
0.6822	Remote Similarity	NPD6684	Approved
0.6818	Remote Similarity	NPD6050	Approved
0.681	Remote Similarity	NPD5174	Approved
0.681	Remote Similarity	NPD5175	Approved
0.6794	Remote Similarity	NPD7260	Phase 2
0.6786	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5223	Approved
0.6774	Remote Similarity	NPD6313	Approved
0.6774	Remote Similarity	NPD7327	Approved
0.6774	Remote Similarity	NPD7328	Approved
0.6774	Remote Similarity	NPD6314	Approved
0.6762	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD5696	Approved
0.6746	Remote Similarity	NPD6908	Approved
0.6746	Remote Similarity	NPD8033	Approved
0.6746	Remote Similarity	NPD6909	Approved
0.6727	Remote Similarity	NPD5692	Phase 3
0.6723	Remote Similarity	NPD4730	Approved
0.6723	Remote Similarity	NPD4729	Approved
0.6697	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6903	Approved
0.6695	Remote Similarity	NPD4767	Approved
0.6695	Remote Similarity	NPD4768	Approved
0.6692	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6641	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD6412	Phase 2
0.6614	Remote Similarity	NPD8378	Approved
0.6614	Remote Similarity	NPD8380	Approved
0.6614	Remote Similarity	NPD8296	Approved
0.6614	Remote Similarity	NPD8379	Approved
0.6614	Remote Similarity	NPD7503	Approved
0.6614	Remote Similarity	NPD8335	Approved
0.6612	Remote Similarity	NPD5249	Phase 3
0.6612	Remote Similarity	NPD5247	Approved
0.6612	Remote Similarity	NPD5250	Approved
0.6612	Remote Similarity	NPD5251	Approved
0.6612	Remote Similarity	NPD5248	Approved
0.6604	Remote Similarity	NPD6435	Approved
0.6583	Remote Similarity	NPD5128	Approved
0.6581	Remote Similarity	NPD7632	Discontinued
0.6577	Remote Similarity	NPD5785	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6525	Remote Similarity	NPD4754	Approved
0.6518	Remote Similarity	NPD7983	Approved
0.6496	Remote Similarity	NPD1700	Approved
0.6493	Remote Similarity	NPD6845	Suspended
0.6484	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD5778	Approved
0.646	Remote Similarity	NPD5779	Approved
0.646	Remote Similarity	NPD6399	Phase 3
0.6455	Remote Similarity	NPD3573	Approved
0.6435	Remote Similarity	NPD5221	Approved
0.6435	Remote Similarity	NPD5222	Approved
0.6435	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5215	Approved
0.6423	Remote Similarity	NPD5216	Approved
0.6423	Remote Similarity	NPD5217	Approved
0.6422	Remote Similarity	NPD5363	Approved
0.6415	Remote Similarity	NPD5368	Approved
0.6404	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7900	Approved
0.6404	Remote Similarity	NPD6001	Approved
0.6379	Remote Similarity	NPD5959	Approved
0.6379	Remote Similarity	NPD5173	Approved
0.6372	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD5786	Approved
0.6357	Remote Similarity	NPD8513	Phase 3
0.6357	Remote Similarity	NPD8515	Approved
0.6357	Remote Similarity	NPD8517	Approved
0.6357	Remote Similarity	NPD6921	Approved
0.6357	Remote Similarity	NPD8516	Approved
0.6348	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5654	Approved
0.6341	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5169	Approved
0.6341	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD5328	Approved
0.6339	Remote Similarity	NPD6051	Approved
0.6339	Remote Similarity	NPD4753	Phase 2
0.6325	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD4202	Approved
0.6306	Remote Similarity	NPD4251	Approved
0.6306	Remote Similarity	NPD4250	Approved
0.6299	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4697	Phase 3
0.629	Remote Similarity	NPD5127	Approved
0.6276	Remote Similarity	NPD7236	Approved
0.6262	Remote Similarity	NPD4821	Approved
0.6262	Remote Similarity	NPD4819	Approved
0.6262	Remote Similarity	NPD4822	Approved
0.6262	Remote Similarity	NPD4820	Approved
0.6262	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5282	Discontinued
0.6261	Remote Similarity	NPD7748	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