NPASS Compound

Structure

CID283081 OpenBabel06191716092D 32 33 0 0 1 0 0 0 0 0999 V2000 -0.8406 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6362 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6068 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3622 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6362 1.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2097 0.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1509 0.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0921 0.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6068 1.6811 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 4.2028 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 0.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8839 1.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5650 -0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0627 0.8406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0921 2.5217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2028 1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7244 1.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4055 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5650 -1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2391 -0.8406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 0.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0433 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 31 1 0 0 0 0 2 6 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 16 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 31 1 0 0 0 0 17 25 2 0 0 0 0 17 32 1 0 0 0 0 18 19 1 6 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.1
Volume:	424.987
LogP:	1.576
LogD:	1.368
LogS:	-2.364
# Rotatable Bonds:	10
TPSA:	191.05
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	3.545
Fsp3:	0.19
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.252
MDCK Permeability:	1.4136409845377784e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.593
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	97.50762939453125%
Volume Distribution (VD):	0.264
Pgp-substrate:	2.608604907989502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.067
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.492
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.321
Half-life (T1/2):	0.96

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.505
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.621
Carcinogencity:	0.069
Eye Corrosion:	0.003
Eye Irritation:	0.174
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC283081

Natural Product ID:	NPC283081
*Common Name:**	Cimicifugic Acid A
IUPAC Name:	(2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxybutanedioic acid
Synonyms:
Standard InCHIKey:	LIJMMUDJSMCVDJ-ZHBFVYIWSA-N
Standard InCHI:	InChI=1S/C21H20O11/c1-31-16-9-11(2-6-14(16)23)4-7-17(25)32-18(19(26)27)21(30,20(28)29)10-12-3-5-13(22)15(24)8-12/h2-9,18,22-24,30H,10H2,1H3,(H,26,27)(H,28,29)/b7-4+/t18-,21-/m1/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@@H]([C@@](C(=O)O)(Cc2ccc(c(c2)O)O)O)C(=O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517537
PubChem CID:	6449879
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
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[11824572]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124775]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562825]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20121210]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO32999	cimicifuga heracleifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192237]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21082802]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21082802]
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]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO525	Actaea racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO30530	Cimicifuga dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
NPO15890	Cimicifuga foetida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO525	Actaea racemosa	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]
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]
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	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	12000.0	nM	PMID[549131]
NPT2	Others	Unspecified		IC50	=	112000.0	nM	PMID[549132]

☑ 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 NPC283081 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	325
0.1-0.2	1304
0.2-0.3	3494
0.3-0.4	7625
0.4-0.5	10218
0.5-0.6	4189
0.6-0.7	7025
0.7-0.8	7690
0.8-0.85	705
0.85-0.9	100
0.9-0.95	13
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299090
1.0	High Similarity	NPC143892
1.0	High Similarity	NPC221383
0.9856	High Similarity	NPC258671
0.9856	High Similarity	NPC53884
0.9784	High Similarity	NPC304956
0.9653	High Similarity	NPC246566
0.9653	High Similarity	NPC95498
0.9496	High Similarity	NPC156709
0.9496	High Similarity	NPC179505
0.9388	High Similarity	NPC477299
0.9357	High Similarity	NPC288452
0.9357	High Similarity	NPC289690
0.9353	High Similarity	NPC279676
0.9353	High Similarity	NPC67349
0.9205	High Similarity	NPC44507
0.92	High Similarity	NPC40920
0.92	High Similarity	NPC223335
0.9184	High Similarity	NPC300329
0.9172	High Similarity	NPC229264
0.9139	High Similarity	NPC469654
0.9116	High Similarity	NPC221091
0.9116	High Similarity	NPC259576
0.9116	High Similarity	NPC32197
0.911	High Similarity	NPC1580
0.9103	High Similarity	NPC98356
0.9	High Similarity	NPC106406
0.898	High Similarity	NPC192568
0.898	High Similarity	NPC471076
0.8966	High Similarity	NPC160378
0.8958	High Similarity	NPC31751
0.8958	High Similarity	NPC253722
0.8958	High Similarity	NPC253481
0.8933	High Similarity	NPC44730
0.8929	High Similarity	NPC168799
0.8929	High Similarity	NPC155209
0.8921	High Similarity	NPC108553
0.8904	High Similarity	NPC223185
0.8889	High Similarity	NPC100675
0.8882	High Similarity	NPC470896
0.8882	High Similarity	NPC473275
0.8881	High Similarity	NPC284409
0.8873	High Similarity	NPC90431
0.8867	High Similarity	NPC163883
0.8867	High Similarity	NPC93498
0.8865	High Similarity	NPC135127
0.8857	High Similarity	NPC5419
0.8857	High Similarity	NPC61
0.8857	High Similarity	NPC25581
0.8857	High Similarity	NPC18074
0.8851	High Similarity	NPC472969
0.8851	High Similarity	NPC98009
0.8849	High Similarity	NPC32626
0.8849	High Similarity	NPC217052
0.8849	High Similarity	NPC237506
0.8849	High Similarity	NPC329344
0.8836	High Similarity	NPC183824
0.8819	High Similarity	NPC147379
0.8819	High Similarity	NPC322021
0.8819	High Similarity	NPC474784
0.8808	High Similarity	NPC146277
0.8808	High Similarity	NPC19380
0.8808	High Similarity	NPC327225
0.8803	High Similarity	NPC113295
0.8803	High Similarity	NPC470990
0.8794	High Similarity	NPC475468
0.8786	High Similarity	NPC198388
0.8784	High Similarity	NPC322660
0.8782	High Similarity	NPC173729
0.8782	High Similarity	NPC134047
0.8782	High Similarity	NPC223006
0.8782	High Similarity	NPC272750
0.8767	High Similarity	NPC285550
0.8742	High Similarity	NPC476434
0.8718	High Similarity	NPC144557
0.8707	High Similarity	NPC474692
0.8693	High Similarity	NPC145425
0.8693	High Similarity	NPC38699
0.869	High Similarity	NPC303683
0.869	High Similarity	NPC295492
0.869	High Similarity	NPC476820
0.869	High Similarity	NPC205751
0.869	High Similarity	NPC476819
0.869	High Similarity	NPC274891
0.869	High Similarity	NPC474875
0.869	High Similarity	NPC26241
0.8675	High Similarity	NPC243891
0.8667	High Similarity	NPC478242
0.8667	High Similarity	NPC125570
0.8667	High Similarity	NPC98809
0.8667	High Similarity	NPC476394
0.8639	High Similarity	NPC258469
0.8639	High Similarity	NPC319628
0.8639	High Similarity	NPC43158
0.8639	High Similarity	NPC472016
0.8639	High Similarity	NPC277315
0.8639	High Similarity	NPC284948
0.8639	High Similarity	NPC37331
0.8639	High Similarity	NPC220664
0.8639	High Similarity	NPC303090
0.8639	High Similarity	NPC192831
0.8621	High Similarity	NPC302857
0.8621	High Similarity	NPC152942
0.8621	High Similarity	NPC219428
0.8621	High Similarity	NPC37250
0.8621	High Similarity	NPC142703
0.8621	High Similarity	NPC278068
0.8618	High Similarity	NPC75695
0.8618	High Similarity	NPC267091
0.8611	High Similarity	NPC471988
0.8601	High Similarity	NPC5310
0.8601	High Similarity	NPC4982
0.8601	High Similarity	NPC68779
0.8601	High Similarity	NPC176814
0.8601	High Similarity	NPC471110
0.8601	High Similarity	NPC300776
0.8582	High Similarity	NPC275724
0.8582	High Similarity	NPC215941
0.8582	High Similarity	NPC137427
0.8582	High Similarity	NPC244246
0.8582	High Similarity	NPC172673
0.8582	High Similarity	NPC123196
0.8582	High Similarity	NPC319282
0.8582	High Similarity	NPC311419
0.8582	High Similarity	NPC65935
0.8581	High Similarity	NPC473090
0.8581	High Similarity	NPC469615
0.8571	High Similarity	NPC297517
0.8571	High Similarity	NPC471027
0.8571	High Similarity	NPC13818
0.8571	High Similarity	NPC206095
0.8571	High Similarity	NPC224389
0.8571	High Similarity	NPC110313
0.8571	High Similarity	NPC131532
0.8571	High Similarity	NPC35702
0.8571	High Similarity	NPC477335
0.8571	High Similarity	NPC476642
0.8571	High Similarity	NPC67467
0.8562	High Similarity	NPC473236
0.8561	High Similarity	NPC120225
0.8561	High Similarity	NPC213552
0.8553	High Similarity	NPC178048
0.8552	High Similarity	NPC281780
0.8552	High Similarity	NPC126206
0.8535	High Similarity	NPC112418
0.8531	High Similarity	NPC327410
0.8526	High Similarity	NPC76211
0.8523	High Similarity	NPC469683
0.8521	High Similarity	NPC469480
0.8521	High Similarity	NPC318799
0.8516	High Similarity	NPC163635
0.8514	High Similarity	NPC477696
0.8514	High Similarity	NPC273657
0.8514	High Similarity	NPC470811
0.8514	High Similarity	NPC106920
0.8514	High Similarity	NPC477697
0.8511	High Similarity	NPC241354
0.8511	High Similarity	NPC83062
0.8511	High Similarity	NPC304622
0.8503	High Similarity	NPC9218
0.8503	High Similarity	NPC477279
0.8503	High Similarity	NPC326065
0.8503	High Similarity	NPC470991
0.85	High Similarity	NPC276466
0.85	High Similarity	NPC151167
0.85	High Similarity	NPC5018
0.85	High Similarity	NPC123722
0.85	High Similarity	NPC123228
0.8489	Intermediate Similarity	NPC280767
0.8489	Intermediate Similarity	NPC289459
0.8489	Intermediate Similarity	NPC132921
0.8487	Intermediate Similarity	NPC473091
0.8483	Intermediate Similarity	NPC471664
0.8483	Intermediate Similarity	NPC471665
0.8481	Intermediate Similarity	NPC471745
0.8472	Intermediate Similarity	NPC67247
0.8471	Intermediate Similarity	NPC130955
0.8471	Intermediate Similarity	NPC471744
0.8471	Intermediate Similarity	NPC472962
0.8471	Intermediate Similarity	NPC472961
0.8467	Intermediate Similarity	NPC9370
0.8467	Intermediate Similarity	NPC287495
0.8462	Intermediate Similarity	NPC239302
0.8462	Intermediate Similarity	NPC226759
0.8456	Intermediate Similarity	NPC46161
0.8456	Intermediate Similarity	NPC239608
0.8451	Intermediate Similarity	NPC142985
0.8451	Intermediate Similarity	NPC195292
0.8447	Intermediate Similarity	NPC186100
0.8447	Intermediate Similarity	NPC216403
0.8447	Intermediate Similarity	NPC41494
0.8446	Intermediate Similarity	NPC140502
0.8446	Intermediate Similarity	NPC477277
0.8446	Intermediate Similarity	NPC477278
0.8446	Intermediate Similarity	NPC52664
0.8442	Intermediate Similarity	NPC295646
0.8442	Intermediate Similarity	NPC199773
0.8431	Intermediate Similarity	NPC32079
0.8429	Intermediate Similarity	NPC168653
0.8429	Intermediate Similarity	NPC251407

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 NPC283081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	824
0.2-0.3	1687
0.3-0.4	2531
0.4-0.5	1966
0.5-0.6	1083
0.6-0.7	612
0.7-0.8	150
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8639	High Similarity	NPD6190	Approved
0.828	Intermediate Similarity	NPD3882	Suspended
0.8217	Intermediate Similarity	NPD3817	Phase 2
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1934	Approved
0.8085	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD6233	Phase 2
0.8	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7988	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6234	Discontinued
0.7945	Intermediate Similarity	NPD6798	Discontinued
0.7939	Intermediate Similarity	NPD3818	Discontinued
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7925	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2801	Approved
0.7922	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7905	Intermediate Similarity	NPD6355	Discontinued
0.7881	Intermediate Similarity	NPD7266	Discontinued
0.7875	Intermediate Similarity	NPD5402	Approved
0.7843	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6799	Approved
0.7798	Intermediate Similarity	NPD6797	Phase 2
0.7798	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD230	Phase 1
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.777	Intermediate Similarity	NPD4062	Phase 3
0.7755	Intermediate Similarity	NPD7095	Approved
0.7751	Intermediate Similarity	NPD7685	Pre-registration
0.7751	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD6801	Discontinued
0.775	Intermediate Similarity	NPD37	Approved
0.774	Intermediate Similarity	NPD9494	Approved
0.7738	Intermediate Similarity	NPD7074	Phase 3
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7716	Intermediate Similarity	NPD4966	Approved
0.7716	Intermediate Similarity	NPD4967	Phase 2
0.7716	Intermediate Similarity	NPD4965	Approved
0.7707	Intermediate Similarity	NPD1512	Approved
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7679	Intermediate Similarity	NPD7054	Approved
0.7658	Intermediate Similarity	NPD5403	Approved
0.7644	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD4380	Phase 2
0.7625	Intermediate Similarity	NPD6599	Discontinued
0.7619	Intermediate Similarity	NPD7228	Approved
0.7613	Intermediate Similarity	NPD4110	Phase 3
0.7613	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1465	Phase 2
0.7589	Intermediate Similarity	NPD5536	Phase 2
0.758	Intermediate Similarity	NPD1511	Approved
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD8127	Discontinued
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD4534	Discontinued
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5844	Phase 1
0.7469	Intermediate Similarity	NPD6385	Approved
0.7469	Intermediate Similarity	NPD6386	Approved
0.7455	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3455	Phase 2
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD228	Approved
0.741	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD2799	Discontinued
0.7403	Intermediate Similarity	NPD7033	Discontinued
0.7378	Intermediate Similarity	NPD7819	Suspended
0.7372	Intermediate Similarity	NPD5958	Discontinued
0.7368	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7355	Intermediate Similarity	NPD2438	Suspended
0.7351	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD3226	Approved
0.7342	Intermediate Similarity	NPD3887	Approved
0.7342	Intermediate Similarity	NPD2354	Approved
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.7338	Intermediate Similarity	NPD7097	Phase 1
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6832	Phase 2
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD4340	Discontinued
0.732	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.729	Intermediate Similarity	NPD1510	Phase 2
0.7279	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7278	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1549	Phase 2
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7255	Intermediate Similarity	NPD1240	Approved
0.7248	Intermediate Similarity	NPD1203	Approved
0.7248	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD1551	Phase 2
0.7244	Intermediate Similarity	NPD6032	Approved
0.7237	Intermediate Similarity	NPD2313	Discontinued
0.7235	Intermediate Similarity	NPD5242	Approved
0.7219	Intermediate Similarity	NPD1247	Approved
0.7211	Intermediate Similarity	NPD1535	Discovery
0.7208	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3146	Approved
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD5647	Approved
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD5763	Approved
0.7186	Intermediate Similarity	NPD7768	Phase 2
0.7181	Intermediate Similarity	NPD1283	Approved
0.7172	Intermediate Similarity	NPD1894	Discontinued
0.7172	Intermediate Similarity	NPD9545	Approved
0.717	Intermediate Similarity	NPD3750	Approved
0.717	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD9269	Phase 2
0.7162	Intermediate Similarity	NPD1481	Phase 2
0.7161	Intermediate Similarity	NPD1607	Approved
0.7161	Intermediate Similarity	NPD6653	Approved
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7159	Intermediate Similarity	NPD8313	Approved
0.7159	Intermediate Similarity	NPD8312	Approved
0.7151	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD7038	Approved
0.7143	Intermediate Similarity	NPD7039	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2796	Approved
0.7126	Intermediate Similarity	NPD5353	Approved
0.7124	Intermediate Similarity	NPD3268	Approved
0.7122	Intermediate Similarity	NPD1358	Approved
0.7099	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2353	Approved
0.7089	Intermediate Similarity	NPD2344	Approved
0.7089	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD17	Approved
0.7072	Intermediate Similarity	NPD7296	Approved
0.707	Intermediate Similarity	NPD4308	Phase 3
0.707	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7066	Intermediate Similarity	NPD7972	Discontinued
0.7055	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD9717	Approved
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7032	Intermediate Similarity	NPD826	Approved
0.7032	Intermediate Similarity	NPD3620	Phase 2
0.7032	Intermediate Similarity	NPD825	Approved
0.7032	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD9570	Approved
0.7024	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3022	Approved
0.7021	Intermediate Similarity	NPD3021	Approved
0.7021	Intermediate Similarity	NPD2067	Discontinued
0.7014	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD2982	Phase 2
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3536	Discontinued
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD5953	Discontinued
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6988	Remote Similarity	NPD7028	Phase 2
0.6981	Remote Similarity	NPD2343	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