NPASS Compound

Structure

CID284409 OpenBabel06191716092D 26 27 0 0 0 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 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 -4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 6 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 14 20 2 0 0 0 0 15 16 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	357.871
LogP:	1.806
LogD:	1.124
LogS:	-3.307
# Rotatable Bonds:	8
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	2.366
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868
MDCK Permeability:	1.4296165318228304e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.493
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.228
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	84.69219207763672%
Volume Distribution (VD):	0.368
Pgp-substrate:	3.694870948791504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.914
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.612
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.823
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.709
CYP2D6-substrate:	0.647
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	15.846
Half-life (T1/2):	0.96

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.849
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.898
Carcinogencity:	0.205
Eye Corrosion:	0.01
Eye Irritation:	0.937
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC284409

Natural Product ID:	NPC284409
*Common Name:**	Cimiracemate A
IUPAC Name:	[3-(3,4-dihydroxyphenyl)-2-oxopropyl] (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	BZBZUGSXRITWQR-QPJJXVBHSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-25-18-6-3-12(9-17(18)23)4-7-19(24)26-11-14(20)8-13-2-5-15(21)16(22)10-13/h2-7,9-10,21-23H,8,11H2,1H3/b7-4+
SMILES:	COc1ccc(/C=C/C(=O)OCC(=O)Cc2ccc(c(c2)O)O)cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076184
PubChem CID:	5315874
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
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17503850]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20121210]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[20184336]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28558206]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32031796]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30451	Cimicifuga simplex	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO389	Actaea heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15373	Actaea dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2727	Actaea simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	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	1
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	47.0	%	PMID[458613]
NPT927	Cell Line	PBMC	Homo sapiens	Inhibition	=	58.0	%	PMID[458613]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	IC50	=	1100.0	nM	PMID[458614]
NPT862	Individual Protein	Epoxide hydratase	Homo sapiens	Inhibition	=	103.8	%	PMID[458614]

☑ 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 NPC284409 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	309
0.1-0.2	1478
0.2-0.3	4028
0.3-0.4	9215
0.4-0.5	8878
0.5-0.6	3727
0.6-0.7	7901
0.7-0.8	6477
0.8-0.85	520
0.85-0.9	150
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9338	High Similarity	NPC289690
0.9338	High Similarity	NPC288452
0.9237	High Similarity	NPC110313
0.916	High Similarity	NPC151167
0.916	High Similarity	NPC123722
0.916	High Similarity	NPC276466
0.916	High Similarity	NPC5018
0.916	High Similarity	NPC123228
0.9118	High Similarity	NPC90431
0.9098	High Similarity	NPC66905
0.9098	High Similarity	NPC172673
0.9084	High Similarity	NPC120225
0.9084	High Similarity	NPC303680
0.9084	High Similarity	NPC84076
0.9084	High Similarity	NPC179777
0.9084	High Similarity	NPC90128
0.9084	High Similarity	NPC213552
0.9023	High Similarity	NPC304622
0.9023	High Similarity	NPC241354
0.9008	High Similarity	NPC280767
0.9008	High Similarity	NPC289459
0.9007	High Similarity	NPC53884
0.9007	High Similarity	NPC258671
0.8971	High Similarity	NPC471110
0.8963	High Similarity	NPC239302
0.8951	High Similarity	NPC98009
0.8936	High Similarity	NPC160378
0.8936	High Similarity	NPC304956
0.8931	High Similarity	NPC246704
0.8897	High Similarity	NPC155209
0.8897	High Similarity	NPC168799
0.8897	High Similarity	NPC475468
0.8889	High Similarity	NPC198388
0.8881	High Similarity	NPC143892
0.8881	High Similarity	NPC299090
0.8881	High Similarity	NPC221383
0.8881	High Similarity	NPC283081
0.8881	High Similarity	NPC83062
0.8864	High Similarity	NPC53305
0.8864	High Similarity	NPC257589
0.8857	High Similarity	NPC326065
0.8855	High Similarity	NPC257976
0.8855	High Similarity	NPC242372
0.8855	High Similarity	NPC164778
0.8855	High Similarity	NPC4181
0.8832	High Similarity	NPC5310
0.8832	High Similarity	NPC300776
0.8832	High Similarity	NPC176814
0.8832	High Similarity	NPC4982
0.8832	High Similarity	NPC68779
0.8824	High Similarity	NPC61
0.8824	High Similarity	NPC18074
0.8824	High Similarity	NPC25581
0.8824	High Similarity	NPC5419
0.8819	High Similarity	NPC472969
0.8811	High Similarity	NPC98356
0.8806	High Similarity	NPC226661
0.8803	High Similarity	NPC473090
0.8797	High Similarity	NPC276014
0.8797	High Similarity	NPC92207
0.8797	High Similarity	NPC127937
0.8788	High Similarity	NPC60517
0.8788	High Similarity	NPC273686
0.8788	High Similarity	NPC312404
0.8788	High Similarity	NPC146886
0.8788	High Similarity	NPC20443
0.8786	High Similarity	NPC474784
0.8779	High Similarity	NPC114298
0.8776	High Similarity	NPC44730
0.8768	High Similarity	NPC139519
0.8759	High Similarity	NPC476394
0.8759	High Similarity	NPC98809
0.8759	High Similarity	NPC129889
0.8759	High Similarity	NPC307006
0.8731	High Similarity	NPC281020
0.8731	High Similarity	NPC16651
0.8731	High Similarity	NPC32163
0.8712	High Similarity	NPC18984
0.8712	High Similarity	NPC106659
0.8712	High Similarity	NPC229084
0.8712	High Similarity	NPC160900
0.8702	High Similarity	NPC194416
0.8702	High Similarity	NPC177291
0.8696	High Similarity	NPC144662
0.8686	High Similarity	NPC111888
0.8686	High Similarity	NPC50763
0.8676	High Similarity	NPC123196
0.8676	High Similarity	NPC215941
0.8676	High Similarity	NPC137427
0.8676	High Similarity	NPC319282
0.8676	High Similarity	NPC275724
0.8676	High Similarity	NPC244246
0.8676	High Similarity	NPC311419
0.8676	High Similarity	NPC65935
0.8671	High Similarity	NPC46880
0.8671	High Similarity	NPC469615
0.8671	High Similarity	NPC239608
0.8671	High Similarity	NPC46161
0.8662	High Similarity	NPC253481
0.8662	High Similarity	NPC31751
0.8662	High Similarity	NPC253722
0.8652	High Similarity	NPC322021
0.8647	High Similarity	NPC288945
0.8639	High Similarity	NPC243891
0.8639	High Similarity	NPC300329
0.8639	High Similarity	NPC475718
0.8633	High Similarity	NPC113295
0.8626	High Similarity	NPC204466
0.8626	High Similarity	NPC60962
0.8626	High Similarity	NPC109083
0.8626	High Similarity	NPC224814
0.8626	High Similarity	NPC189844
0.8626	High Similarity	NPC14007
0.8626	High Similarity	NPC269843
0.8626	High Similarity	NPC158949
0.8623	High Similarity	NPC159418
0.8623	High Similarity	NPC283823
0.8611	High Similarity	NPC469683
0.8601	High Similarity	NPC192597
0.8601	High Similarity	NPC229218
0.8601	High Similarity	NPC176030
0.8601	High Similarity	NPC141817
0.8601	High Similarity	NPC169214
0.86	High Similarity	NPC470896
0.86	High Similarity	NPC473275
0.8592	High Similarity	NPC477279
0.8592	High Similarity	NPC28398
0.8582	High Similarity	NPC3221
0.8582	High Similarity	NPC325625
0.8581	High Similarity	NPC267091
0.8581	High Similarity	NPC93498
0.8581	High Similarity	NPC95498
0.8581	High Similarity	NPC246566
0.8581	High Similarity	NPC75695
0.8581	High Similarity	NPC163883
0.8571	High Similarity	NPC221091
0.8571	High Similarity	NPC259576
0.8571	High Similarity	NPC163083
0.8561	High Similarity	NPC135127
0.8561	High Similarity	NPC201777
0.8561	High Similarity	NPC70752
0.8552	High Similarity	NPC9370
0.8552	High Similarity	NPC287495
0.855	High Similarity	NPC202474
0.8533	High Similarity	NPC145425
0.8531	High Similarity	NPC477278
0.8531	High Similarity	NPC477277
0.8531	High Similarity	NPC110419
0.8529	High Similarity	NPC2596
0.8529	High Similarity	NPC478215
0.8523	High Similarity	NPC146277
0.8523	High Similarity	NPC19380
0.8514	High Similarity	NPC58310
0.8514	High Similarity	NPC295977
0.8514	High Similarity	NPC178048
0.8511	High Similarity	NPC67349
0.8511	High Similarity	NPC279676
0.8507	High Similarity	NPC85565
0.8503	High Similarity	NPC474556
0.85	High Similarity	NPC204592
0.8496	Intermediate Similarity	NPC286573
0.8493	Intermediate Similarity	NPC229264
0.8489	Intermediate Similarity	NPC327410
0.8485	Intermediate Similarity	NPC470849
0.8485	Intermediate Similarity	NPC470848
0.8483	Intermediate Similarity	NPC207732
0.8477	Intermediate Similarity	NPC471405
0.8473	Intermediate Similarity	NPC141791
0.8473	Intermediate Similarity	NPC263386
0.8473	Intermediate Similarity	NPC299406
0.8472	Intermediate Similarity	NPC312256
0.8467	Intermediate Similarity	NPC477299
0.8467	Intermediate Similarity	NPC469888
0.8462	Intermediate Similarity	NPC100675
0.8462	Intermediate Similarity	NPC29599
0.8462	Intermediate Similarity	NPC166137
0.8462	Intermediate Similarity	NPC282291
0.8456	Intermediate Similarity	NPC293641
0.8456	Intermediate Similarity	NPC203719
0.8456	Intermediate Similarity	NPC12022
0.8456	Intermediate Similarity	NPC117237
0.8456	Intermediate Similarity	NPC20404
0.8456	Intermediate Similarity	NPC472838
0.8456	Intermediate Similarity	NPC20287
0.8456	Intermediate Similarity	NPC306011
0.8446	Intermediate Similarity	NPC473091
0.8446	Intermediate Similarity	NPC261322
0.8444	Intermediate Similarity	NPC87113
0.844	Intermediate Similarity	NPC120852
0.844	Intermediate Similarity	NPC324929
0.8435	Intermediate Similarity	NPC58373
0.8435	Intermediate Similarity	NPC471076
0.8435	Intermediate Similarity	NPC1580
0.8435	Intermediate Similarity	NPC192568
0.8435	Intermediate Similarity	NPC294972
0.8429	Intermediate Similarity	NPC106406
0.8425	Intermediate Similarity	NPC157133
0.8425	Intermediate Similarity	NPC287275
0.8421	Intermediate Similarity	NPC35598
0.8421	Intermediate Similarity	NPC222689

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 NPC284409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	903
0.2-0.3	1570
0.3-0.4	2500
0.4-0.5	1975
0.5-0.6	1110
0.6-0.7	636
0.7-0.8	167
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8712	High Similarity	NPD4379	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD3882	Suspended
0.8456	Intermediate Similarity	NPD9494	Approved
0.8356	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD6190	Approved
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD5536	Phase 2
0.8151	Intermediate Similarity	NPD4628	Phase 3
0.8143	Intermediate Similarity	NPD6798	Discontinued
0.8108	Intermediate Similarity	NPD6799	Approved
0.8099	Intermediate Similarity	NPD6355	Discontinued
0.8085	Intermediate Similarity	NPD4062	Phase 3
0.8085	Intermediate Similarity	NPD6233	Phase 2
0.8039	Intermediate Similarity	NPD1934	Approved
0.8028	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2801	Approved
0.7973	Intermediate Similarity	NPD2354	Approved
0.7972	Intermediate Similarity	NPD230	Phase 1
0.7949	Intermediate Similarity	NPD7075	Discontinued
0.7943	Intermediate Similarity	NPD7095	Approved
0.7905	Intermediate Similarity	NPD8166	Discontinued
0.7881	Intermediate Similarity	NPD1512	Approved
0.7877	Intermediate Similarity	NPD2935	Discontinued
0.7875	Intermediate Similarity	NPD6166	Phase 2
0.7875	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD228	Approved
0.7852	Intermediate Similarity	NPD3887	Approved
0.7843	Intermediate Similarity	NPD3455	Phase 2
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6599	Discontinued
0.7785	Intermediate Similarity	NPD4110	Phase 3
0.7785	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1511	Approved
0.7744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6797	Phase 2
0.7742	Intermediate Similarity	NPD6385	Approved
0.7742	Intermediate Similarity	NPD6386	Approved
0.7724	Intermediate Similarity	NPD447	Suspended
0.7721	Intermediate Similarity	NPD9545	Approved
0.7703	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2353	Approved
0.7698	Intermediate Similarity	NPD1608	Approved
0.7697	Intermediate Similarity	NPD7251	Discontinued
0.7697	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3146	Approved
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.7692	Intermediate Similarity	NPD3027	Phase 3
0.7669	Intermediate Similarity	NPD3818	Discontinued
0.7651	Intermediate Similarity	NPD7808	Phase 3
0.7651	Intermediate Similarity	NPD4534	Discontinued
0.7639	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7054	Approved
0.7613	Intermediate Similarity	NPD7458	Discontinued
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7612	Intermediate Similarity	NPD5283	Phase 1
0.7593	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1894	Discontinued
0.759	Intermediate Similarity	NPD7685	Pre-registration
0.7589	Intermediate Similarity	NPD1283	Approved
0.7584	Intermediate Similarity	NPD7266	Discontinued
0.7576	Intermediate Similarity	NPD7472	Approved
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7571	Intermediate Similarity	NPD3972	Approved
0.7571	Intermediate Similarity	NPD1481	Phase 2
0.7568	Intermediate Similarity	NPD2799	Discontinued
0.7562	Intermediate Similarity	NPD919	Approved
0.7557	Intermediate Similarity	NPD1358	Approved
0.7533	Intermediate Similarity	NPD5958	Discontinued
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD5049	Phase 3
0.7531	Intermediate Similarity	NPD6232	Discontinued
0.7517	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3268	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD1535	Discovery
0.75	Intermediate Similarity	NPD7473	Discontinued
0.7484	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD5403	Approved
0.7483	Intermediate Similarity	NPD4340	Discontinued
0.7483	Intermediate Similarity	NPD1933	Approved
0.7482	Intermediate Similarity	NPD17	Approved
0.7468	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6234	Discontinued
0.7452	Intermediate Similarity	NPD4380	Phase 2
0.745	Intermediate Similarity	NPD1510	Phase 2
0.7429	Intermediate Similarity	NPD3847	Discontinued
0.7426	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7819	Suspended
0.7417	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2979	Phase 3
0.7415	Intermediate Similarity	NPD943	Approved
0.7415	Intermediate Similarity	NPD1240	Approved
0.7413	Intermediate Similarity	NPD1203	Approved
0.7413	Intermediate Similarity	NPD2797	Approved
0.74	Intermediate Similarity	NPD2438	Suspended
0.7384	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6832	Phase 2
0.7376	Intermediate Similarity	NPD1281	Approved
0.7362	Intermediate Similarity	NPD7199	Phase 2
0.7355	Intermediate Similarity	NPD5401	Approved
0.7351	Intermediate Similarity	NPD2344	Approved
0.7348	Intermediate Similarity	NPD3134	Approved
0.7324	Intermediate Similarity	NPD9269	Phase 2
0.732	Intermediate Similarity	NPD3750	Approved
0.7315	Intermediate Similarity	NPD1607	Approved
0.7313	Intermediate Similarity	NPD3021	Approved
0.7313	Intermediate Similarity	NPD3022	Approved
0.7312	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6273	Approved
0.7305	Intermediate Similarity	NPD3496	Discontinued
0.7303	Intermediate Similarity	NPD1549	Phase 2
0.7297	Intermediate Similarity	NPD826	Approved
0.7297	Intermediate Similarity	NPD825	Approved
0.7296	Intermediate Similarity	NPD7411	Suspended
0.7296	Intermediate Similarity	NPD6873	Phase 2
0.7294	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5585	Approved
0.7286	Intermediate Similarity	NPD1651	Approved
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2313	Discontinued
0.7279	Intermediate Similarity	NPD3764	Approved
0.7278	Intermediate Similarity	NPD824	Approved
0.7273	Intermediate Similarity	NPD5242	Approved
0.7256	Intermediate Similarity	NPD8127	Discontinued
0.7256	Intermediate Similarity	NPD2821	Approved
0.725	Intermediate Similarity	NPD37	Approved
0.7248	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5647	Approved
0.7241	Intermediate Similarity	NPD2798	Approved
0.7237	Intermediate Similarity	NPD2346	Discontinued
0.7237	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4626	Approved
0.7234	Intermediate Similarity	NPD1778	Approved
0.7233	Intermediate Similarity	NPD7028	Phase 2
0.7226	Intermediate Similarity	NPD7440	Discontinued
0.7222	Intermediate Similarity	NPD4965	Approved
0.7222	Intermediate Similarity	NPD1876	Approved
0.7222	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD4308	Phase 3
0.7216	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1653	Approved
0.7208	Intermediate Similarity	NPD7003	Approved
0.7203	Intermediate Similarity	NPD9717	Approved
0.7202	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6653	Approved
0.7195	Intermediate Similarity	NPD5494	Approved
0.7188	Intermediate Similarity	NPD958	Approved
0.7181	Intermediate Similarity	NPD1613	Approved
0.7181	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3620	Phase 2
0.7176	Intermediate Similarity	NPD7038	Approved
0.7176	Intermediate Similarity	NPD7039	Approved
0.7174	Intermediate Similarity	NPD2629	Approved
0.7172	Intermediate Similarity	NPD3266	Approved
0.7172	Intermediate Similarity	NPD3267	Approved
0.7171	Intermediate Similarity	NPD4476	Approved
0.7171	Intermediate Similarity	NPD1551	Phase 2
0.7171	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD2796	Approved
0.7171	Intermediate Similarity	NPD2531	Phase 2
0.7169	Intermediate Similarity	NPD3926	Phase 2
0.7163	Intermediate Similarity	NPD1357	Approved
0.7163	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD2309	Approved
0.716	Intermediate Similarity	NPD5353	Approved
0.7153	Intermediate Similarity	NPD5535	Approved
0.7152	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD2163	Approved
0.7143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD2614	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD555	Phase 2
0.7124	Intermediate Similarity	NPD5762	Approved
0.7124	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2684	Approved
0.7105	Intermediate Similarity	NPD7033	Discontinued
0.7105	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3225	Approved
0.7102	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3274	Phase 2
0.7078	Intermediate Similarity	NPD2897	Discontinued
0.7075	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD9493	Approved
0.707	Intermediate Similarity	NPD4357	Discontinued
0.7067	Intermediate Similarity	NPD3142	Approved
0.7067	Intermediate Similarity	NPD3140	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