NPASS Compound

Structure

NPC43627 OpenBabel07101718302D 22 23 0 0 1 0 0 0 0 0999 V2000 -0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 -0.0000 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 1 0 0 0 0 5 8 1 0 0 0 0 6 10 2 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 1 1 6 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 15 19 2 0 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.14
Volume:	319.477
LogP:	3.446
LogD:	2.769
LogS:	-4.104
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.589
Synthetic Accessibility Score:	3.902
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
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:	1.974039332708344e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	98.36219787597656%
Volume Distribution (VD):	0.311
Pgp-substrate:	1.475000023841858%

ADMET: Metabolism

CYP1A2-inhibitor:	0.738
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.676
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.622
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.695
CYP2D6-substrate:	0.541
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	7.437
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.74
Skin Sensitization:	0.93
Carcinogencity:	0.892
Eye Corrosion:	0.264
Eye Irritation:	0.774
Respiratory Toxicity:	0.718

Download Data

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

Natural Product: NPC43627

Natural Product ID:	NPC43627
*Common Name:**	Monocillin Ii
IUPAC Name:	(4E,8E,11S)-15-hydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),4,8,15,17-pentaene-3,13-dione
Synonyms:	Monocillin II
Standard InCHIKey:	LSIFWWADIGESKN-UIWFPMPVSA-N
Standard InCHI:	InChI=1S/C18H20O4/c1-13-8-5-3-2-4-6-10-15(19)12-14-9-7-11-16(20)17(14)18(21)22-13/h3,5-7,9-11,13,20H,2,4,8,12H2,1H3/b5-3+,10-6+/t13-/m0/s1
SMILES:	C[C@H]1C/C=C/CC/C=C/C(=O)Cc2cccc(c2C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498851
PubChem CID:	6478915
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO33698	Paecilomyces sp. SC0926	Species		Eukaryota	n.a.	Dinghu Mountain Biosphere Reserve, Guangdong, China	2003-MAR	PMID[28749671]

☑ 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	1
Others	6

Activity Type	# Activity
Individual Protein	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual Protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	14.8	%	PMID[526274]
NPT232	Individual Protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	26.2	%	PMID[526274]
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	Inhibition	=	63.5	%	PMID[526274]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	Inhibition	=	9.0	%	PMID[526274]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	Inhibition	=	-3.1	%	PMID[526274]
NPT2	Others	Unspecified		IC50	=	7360.0	nM	PMID[526273]
NPT27	Others	Unspecified		TC50	=	17.62	uM	PMID[526273]

☑ 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 NPC43627 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	288
0.1-0.2	1303
0.2-0.3	3402
0.3-0.4	7897
0.4-0.5	10962
0.5-0.6	4474
0.6-0.7	8381
0.7-0.8	5486
0.8-0.85	356
0.85-0.9	128
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC474097
0.9403	High Similarity	NPC478201
0.9403	High Similarity	NPC472035
0.9259	High Similarity	NPC478217
0.9259	High Similarity	NPC313123
0.9242	High Similarity	NPC27407
0.9197	High Similarity	NPC126882
0.9197	High Similarity	NPC210966
0.9197	High Similarity	NPC478203
0.9179	High Similarity	NPC9121
0.9179	High Similarity	NPC177307
0.9179	High Similarity	NPC33144
0.9179	High Similarity	NPC478200
0.913	High Similarity	NPC472034
0.913	High Similarity	NPC257558
0.9124	High Similarity	NPC478202
0.9098	High Similarity	NPC142027
0.9084	High Similarity	NPC214702
0.9084	High Similarity	NPC470831
0.9084	High Similarity	NPC7012
0.9065	High Similarity	NPC472033
0.9037	High Similarity	NPC191835
0.9037	High Similarity	NPC472403
0.9	High Similarity	NPC472036
0.8963	High Similarity	NPC474771
0.8963	High Similarity	NPC474849
0.8963	High Similarity	NPC70380
0.8963	High Similarity	NPC65837
0.8963	High Similarity	NPC149372
0.8963	High Similarity	NPC71256
0.8963	High Similarity	NPC178467
0.8915	High Similarity	NPC167055
0.8915	High Similarity	NPC240744
0.8905	High Similarity	NPC158472
0.8897	High Similarity	NPC94248
0.8897	High Similarity	NPC475974
0.8897	High Similarity	NPC221104
0.8897	High Similarity	NPC212693
0.8872	High Similarity	NPC470160
0.8841	High Similarity	NPC158634
0.8841	High Similarity	NPC470842
0.8837	High Similarity	NPC91475
0.8837	High Similarity	NPC265910
0.8832	High Similarity	NPC52358
0.8832	High Similarity	NPC92655
0.881	High Similarity	NPC90522
0.881	High Similarity	NPC328459
0.8806	High Similarity	NPC153783
0.8777	High Similarity	NPC474385
0.8759	High Similarity	NPC197666
0.8759	High Similarity	NPC126739
0.8759	High Similarity	NPC472602
0.875	High Similarity	NPC235115
0.875	High Similarity	NPC291454
0.874	High Similarity	NPC72977
0.873	High Similarity	NPC94637
0.8714	High Similarity	NPC472006
0.8714	High Similarity	NPC66593
0.8712	High Similarity	NPC95537
0.8705	High Similarity	NPC1704
0.8705	High Similarity	NPC53649
0.8705	High Similarity	NPC472603
0.8705	High Similarity	NPC244923
0.8705	High Similarity	NPC475730
0.8705	High Similarity	NPC67650
0.8696	High Similarity	NPC105456
0.8696	High Similarity	NPC268052
0.8696	High Similarity	NPC32360
0.8696	High Similarity	NPC295339
0.8696	High Similarity	NPC474655
0.8696	High Similarity	NPC139634
0.8686	High Similarity	NPC301915
0.8686	High Similarity	NPC261292
0.8682	High Similarity	NPC217756
0.8672	High Similarity	NPC301987
0.8672	High Similarity	NPC292665
0.8672	High Similarity	NPC26433
0.8672	High Similarity	NPC35856
0.8672	High Similarity	NPC178395
0.8672	High Similarity	NPC115188
0.8672	High Similarity	NPC179092
0.8672	High Similarity	NPC159760
0.8672	High Similarity	NPC272454
0.8672	High Similarity	NPC244994
0.8672	High Similarity	NPC222876
0.8671	High Similarity	NPC471642
0.8671	High Similarity	NPC240253
0.8671	High Similarity	NPC73411
0.8671	High Similarity	NPC240622
0.8671	High Similarity	NPC471641
0.8671	High Similarity	NPC215711
0.8667	High Similarity	NPC295406
0.8667	High Similarity	NPC289572
0.8667	High Similarity	NPC200422
0.8667	High Similarity	NPC157478
0.8661	High Similarity	NPC233165
0.8661	High Similarity	NPC184579
0.8657	High Similarity	NPC219892
0.8657	High Similarity	NPC189823
0.8652	High Similarity	NPC86373
0.8652	High Similarity	NPC280404
0.8652	High Similarity	NPC42540
0.8652	High Similarity	NPC151607
0.8652	High Similarity	NPC277426
0.8652	High Similarity	NPC210425
0.8651	High Similarity	NPC125252
0.8636	High Similarity	NPC181715
0.8633	High Similarity	NPC472601
0.8633	High Similarity	NPC472600
0.8623	High Similarity	NPC61590
0.8601	High Similarity	NPC210320
0.8593	High Similarity	NPC477406
0.8592	High Similarity	NPC312789
0.8592	High Similarity	NPC83272
0.8582	High Similarity	NPC159721
0.8582	High Similarity	NPC51106
0.8582	High Similarity	NPC354984
0.8571	High Similarity	NPC472605
0.8571	High Similarity	NPC472604
0.8571	High Similarity	NPC41263
0.8571	High Similarity	NPC257003
0.8571	High Similarity	NPC128825
0.8561	High Similarity	NPC299405
0.8561	High Similarity	NPC111422
0.8561	High Similarity	NPC306835
0.8561	High Similarity	NPC471602
0.8561	High Similarity	NPC256463
0.8561	High Similarity	NPC216312
0.8561	High Similarity	NPC476477
0.8561	High Similarity	NPC29771
0.8552	High Similarity	NPC56204
0.8551	High Similarity	NPC194579
0.8551	High Similarity	NPC135837
0.854	High Similarity	NPC267539
0.854	High Similarity	NPC229638
0.854	High Similarity	NPC254832
0.854	High Similarity	NPC204257
0.854	High Similarity	NPC71108
0.854	High Similarity	NPC176102
0.854	High Similarity	NPC29317
0.8531	High Similarity	NPC107625
0.85	High Similarity	NPC155205
0.85	High Similarity	NPC37992
0.85	High Similarity	NPC32749
0.85	High Similarity	NPC220496
0.85	High Similarity	NPC42262
0.85	High Similarity	NPC241349
0.85	High Similarity	NPC327916
0.85	High Similarity	NPC147542
0.8483	Intermediate Similarity	NPC84142
0.8467	Intermediate Similarity	NPC175943
0.8451	Intermediate Similarity	NPC471731
0.8451	Intermediate Similarity	NPC472610
0.8451	Intermediate Similarity	NPC476473
0.8451	Intermediate Similarity	NPC469542
0.8451	Intermediate Similarity	NPC21873
0.845	Intermediate Similarity	NPC233282
0.8444	Intermediate Similarity	NPC17840
0.8444	Intermediate Similarity	NPC247477
0.8444	Intermediate Similarity	NPC473271
0.844	Intermediate Similarity	NPC37530
0.844	Intermediate Similarity	NPC149533
0.844	Intermediate Similarity	NPC130485
0.844	Intermediate Similarity	NPC471444
0.8429	Intermediate Similarity	NPC88269
0.8425	Intermediate Similarity	NPC477453
0.8425	Intermediate Similarity	NPC472891
0.8425	Intermediate Similarity	NPC164762
0.8414	Intermediate Similarity	NPC153417
0.8409	Intermediate Similarity	NPC470163
0.8409	Intermediate Similarity	NPC470162
0.8406	Intermediate Similarity	NPC182496
0.8406	Intermediate Similarity	NPC180905
0.8403	Intermediate Similarity	NPC473023
0.8397	Intermediate Similarity	NPC244351
0.8397	Intermediate Similarity	NPC46634
0.8397	Intermediate Similarity	NPC477151
0.8397	Intermediate Similarity	NPC132518
0.8394	Intermediate Similarity	NPC472591
0.8392	Intermediate Similarity	NPC274085
0.8392	Intermediate Similarity	NPC103910
0.8392	Intermediate Similarity	NPC89664
0.838	Intermediate Similarity	NPC469579
0.838	Intermediate Similarity	NPC471644
0.838	Intermediate Similarity	NPC250755
0.838	Intermediate Similarity	NPC471640
0.838	Intermediate Similarity	NPC474300
0.838	Intermediate Similarity	NPC471733
0.8369	Intermediate Similarity	NPC168471
0.8369	Intermediate Similarity	NPC315578
0.8369	Intermediate Similarity	NPC99441
0.8367	Intermediate Similarity	NPC91809
0.8358	Intermediate Similarity	NPC71525
0.8357	Intermediate Similarity	NPC4214
0.8356	Intermediate Similarity	NPC476684
0.8346	Intermediate Similarity	NPC287473
0.8346	Intermediate Similarity	NPC262671
0.8346	Intermediate Similarity	NPC4164
0.8346	Intermediate Similarity	NPC201728
0.8345	Intermediate Similarity	NPC14098

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 NPC43627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	887
0.2-0.3	1585
0.3-0.4	2518
0.4-0.5	2063
0.5-0.6	1238
0.6-0.7	475
0.7-0.8	125
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD9493	Approved
0.8298	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD2935	Discontinued
0.812	Intermediate Similarity	NPD9717	Approved
0.8015	Intermediate Similarity	NPD9545	Approved
0.8013	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2532	Approved
0.7959	Intermediate Similarity	NPD2533	Approved
0.7959	Intermediate Similarity	NPD2534	Approved
0.7941	Intermediate Similarity	NPD1203	Approved
0.7937	Intermediate Similarity	NPD9266	Approved
0.7937	Intermediate Similarity	NPD74	Approved
0.7914	Intermediate Similarity	NPD411	Approved
0.7899	Intermediate Similarity	NPD6832	Phase 2
0.7872	Intermediate Similarity	NPD447	Suspended
0.7867	Intermediate Similarity	NPD3226	Approved
0.7857	Intermediate Similarity	NPD9267	Approved
0.7857	Intermediate Similarity	NPD9264	Approved
0.7857	Intermediate Similarity	NPD9263	Approved
0.7847	Intermediate Similarity	NPD2346	Discontinued
0.7808	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD3268	Approved
0.7763	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1510	Phase 2
0.7708	Intermediate Similarity	NPD2799	Discontinued
0.7681	Intermediate Similarity	NPD1470	Approved
0.7676	Intermediate Similarity	NPD1240	Approved
0.7671	Intermediate Similarity	NPD1549	Phase 2
0.7655	Intermediate Similarity	NPD1551	Phase 2
0.7655	Intermediate Similarity	NPD5404	Approved
0.7655	Intermediate Similarity	NPD5406	Approved
0.7655	Intermediate Similarity	NPD5405	Approved
0.7655	Intermediate Similarity	NPD5408	Approved
0.7651	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD1201	Approved
0.7632	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7075	Discontinued
0.7626	Intermediate Similarity	NPD1019	Discontinued
0.7626	Intermediate Similarity	NPD2798	Approved
0.7613	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD9281	Approved
0.7569	Intermediate Similarity	NPD1607	Approved
0.7568	Intermediate Similarity	NPD3750	Approved
0.7562	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1164	Approved
0.7548	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD9261	Approved
0.7538	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7535	Intermediate Similarity	NPD2313	Discontinued
0.7534	Intermediate Similarity	NPD2796	Approved
0.7519	Intermediate Similarity	NPD2182	Approved
0.7484	Intermediate Similarity	NPD1934	Approved
0.7483	Intermediate Similarity	NPD520	Approved
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6599	Discontinued
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7452	Intermediate Similarity	NPD3882	Suspended
0.745	Intermediate Similarity	NPD4628	Phase 3
0.7438	Intermediate Similarity	NPD6232	Discontinued
0.7431	Intermediate Similarity	NPD943	Approved
0.7429	Intermediate Similarity	NPD3267	Approved
0.7429	Intermediate Similarity	NPD2797	Approved
0.7429	Intermediate Similarity	NPD3266	Approved
0.7407	Intermediate Similarity	NPD7473	Discontinued
0.7405	Intermediate Similarity	NPD3749	Approved
0.7391	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5402	Approved
0.7389	Intermediate Similarity	NPD3817	Phase 2
0.7386	Intermediate Similarity	NPD5403	Approved
0.7381	Intermediate Similarity	NPD8150	Discontinued
0.7375	Intermediate Similarity	NPD6959	Discontinued
0.7372	Intermediate Similarity	NPD6801	Discontinued
0.7372	Intermediate Similarity	NPD4626	Approved
0.7347	Intermediate Similarity	NPD4308	Phase 3
0.7342	Intermediate Similarity	NPD7768	Phase 2
0.7325	Intermediate Similarity	NPD2801	Approved
0.7319	Intermediate Similarity	NPD3496	Discontinued
0.7308	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1511	Approved
0.7303	Intermediate Similarity	NPD7390	Discontinued
0.7299	Intermediate Similarity	NPD5691	Approved
0.7299	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2309	Approved
0.726	Intermediate Similarity	NPD1933	Approved
0.7255	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1471	Phase 3
0.7246	Intermediate Similarity	NPD1778	Approved
0.7233	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3748	Approved
0.723	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD5710	Approved
0.7222	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD8166	Discontinued
0.7214	Intermediate Similarity	NPD1608	Approved
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7209	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD164	Approved
0.7208	Intermediate Similarity	NPD1512	Approved
0.7208	Intermediate Similarity	NPD6273	Approved
0.7203	Intermediate Similarity	NPD9494	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5647	Approved
0.7133	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6663	Approved
0.7117	Intermediate Similarity	NPD6808	Phase 2
0.7113	Intermediate Similarity	NPD3225	Approved
0.7113	Intermediate Similarity	NPD1283	Approved
0.7108	Intermediate Similarity	NPD7054	Approved
0.7103	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8313	Approved
0.7101	Intermediate Similarity	NPD8312	Approved
0.7092	Intermediate Similarity	NPD3972	Approved
0.7092	Intermediate Similarity	NPD9269	Phase 2
0.7089	Intermediate Similarity	NPD5889	Approved
0.7089	Intermediate Similarity	NPD5890	Approved
0.7083	Intermediate Similarity	NPD5736	Approved
0.7075	Intermediate Similarity	NPD4060	Phase 1
0.7075	Intermediate Similarity	NPD4307	Phase 2
0.707	Intermediate Similarity	NPD3455	Phase 2
0.7067	Intermediate Similarity	NPD6100	Approved
0.7067	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD7074	Phase 3
0.7066	Intermediate Similarity	NPD7472	Approved
0.7059	Intermediate Similarity	NPD6190	Approved
0.7055	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD920	Approved
0.705	Intermediate Similarity	NPD9268	Approved
0.7044	Intermediate Similarity	NPD6844	Discontinued
0.7041	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2800	Approved
0.7039	Intermediate Similarity	NPD1243	Approved
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7024	Intermediate Similarity	NPD5953	Discontinued
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7013	Intermediate Similarity	NPD7236	Approved
0.7013	Intermediate Similarity	NPD3300	Phase 2
0.7013	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD1876	Approved
0.6986	Remote Similarity	NPD7008	Discontinued
0.6985	Remote Similarity	NPD1241	Discontinued
0.6982	Remote Similarity	NPD7251	Discontinued
0.6982	Remote Similarity	NPD6559	Discontinued
0.698	Remote Similarity	NPD6653	Approved
0.698	Remote Similarity	NPD6651	Approved
0.6963	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2651	Approved
0.6962	Remote Similarity	NPD2649	Approved
0.6959	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD4477	Approved
0.6954	Remote Similarity	NPD4476	Approved
0.6954	Remote Similarity	NPD2438	Suspended
0.6946	Remote Similarity	NPD7177	Discontinued
0.6941	Remote Similarity	NPD7808	Phase 3
0.6939	Remote Similarity	NPD6798	Discontinued
0.6934	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6585	Discontinued
0.6908	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6004	Phase 3
0.6908	Remote Similarity	NPD6005	Phase 3
0.6908	Remote Similarity	NPD6002	Phase 3
0.6908	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7286	Phase 2
0.6901	Remote Similarity	NPD1281	Approved
0.6899	Remote Similarity	NPD1238	Approved
0.6894	Remote Similarity	NPD1465	Phase 2
0.6879	Remote Similarity	NPD3019	Approved
0.6879	Remote Similarity	NPD2932	Approved
0.6875	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6213	Phase 3
0.6875	Remote Similarity	NPD6212	Phase 3
0.687	Remote Similarity	NPD6647	Phase 2
0.6866	Remote Similarity	NPD6831	Clinical (unspecified phase)

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