NPASS Compound

Structure

CID184053 OpenBabel06191715562D 26 27 0 0 1 0 0 0 0 0999 V2000 4.7991 4.1402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3508 5.8132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 -1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8672 3.6225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 0.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1260 4.5884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 3.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3496 1.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 1.1248 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0920 4.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6425 2.3978 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 19 26 1 0 0 0 0 20 22 1 6 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 4 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	391.297
LogP:	5.435
LogD:	3.897
LogS:	-3.695
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	3.656
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	2.0234889234416187e-05
Pgp-inhibitor:	0.396
Pgp-substrate:	0.263
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.069
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	99.49308013916016%
Volume Distribution (VD):	0.232
Pgp-substrate:	2.7827701568603516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.246
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.377
CYP2C9-substrate:	0.422
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	4.446
Half-life (T1/2):	0.624

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.89
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.46
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.117
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC184053

Natural Product ID:	NPC184053
*Common Name:**	Kuhistanol D
IUPAC Name:	(2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3-hydroxy-2-methyl-3,4-dihydrochromene-6-carboxylic acid
Synonyms:	kuhistanol D
Standard InCHIKey:	KSXMPLFGEDQAEG-BCVDLSEWSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-15(2)7-5-8-16(3)9-6-12-22(4)20(23)14-18-13-17(21(24)25)10-11-19(18)26-22/h7,9-11,13,20,23H,5-6,8,12,14H2,1-4H3,(H,24,25)/b16-9+/t20-,22-/m1/s1
SMILES:	C/C(=CCC[C@@]1(C)Oc2ccc(cc2C[C@H]1O)C(=O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526664
PubChem CID:	10338460
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO24669	Ferula kuhistanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757719]
NPO24669	Ferula kuhistanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350156]
NPO24669	Ferula kuhistanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24669	Ferula kuhistanica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	70.3	%	PMID[545630]
NPT2	Others	Unspecified	Inhibition	=	77.3	%	PMID[545630]
NPT2	Others	Unspecified	Inhibition	=	61.8	%	PMID[545630]

☑ 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 NPC184053 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	1252
0.2-0.3	2955
0.3-0.4	6908
0.4-0.5	10903
0.5-0.6	4736
0.6-0.7	5830
0.7-0.8	8566
0.8-0.85	1094
0.85-0.9	134
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9179	High Similarity	NPC109778
0.9155	High Similarity	NPC474044
0.9111	High Similarity	NPC473777
0.911	High Similarity	NPC256141
0.9044	High Similarity	NPC302844
0.9037	High Similarity	NPC327457
0.9037	High Similarity	NPC86774
0.9034	High Similarity	NPC88886
0.9034	High Similarity	NPC104172
0.9	High Similarity	NPC473988
0.8973	High Similarity	NPC180351
0.8955	High Similarity	NPC473993
0.8955	High Similarity	NPC121104
0.8951	High Similarity	NPC213900
0.8912	High Similarity	NPC244577
0.8912	High Similarity	NPC472420
0.8912	High Similarity	NPC472422
0.8912	High Similarity	NPC471676
0.8912	High Similarity	NPC263384
0.8897	High Similarity	NPC473133
0.8897	High Similarity	NPC470670
0.8897	High Similarity	NPC47388
0.8897	High Similarity	NPC66991
0.8897	High Similarity	NPC91902
0.8897	High Similarity	NPC14875
0.8889	High Similarity	NPC2401
0.8889	High Similarity	NPC473744
0.8881	High Similarity	NPC473090
0.8828	High Similarity	NPC286038
0.8828	High Similarity	NPC474302
0.8819	High Similarity	NPC113397
0.8815	High Similarity	NPC37512
0.8803	High Similarity	NPC195357
0.8803	High Similarity	NPC469911
0.8803	High Similarity	NPC152771
0.8794	High Similarity	NPC151946
0.8792	High Similarity	NPC7989
0.8792	High Similarity	NPC472583
0.8792	High Similarity	NPC223701
0.8784	High Similarity	NPC48671
0.8784	High Similarity	NPC474772
0.8784	High Similarity	NPC472423
0.8784	High Similarity	NPC474744
0.8784	High Similarity	NPC471677
0.8776	High Similarity	NPC103116
0.8767	High Similarity	NPC85773
0.8759	High Similarity	NPC171656
0.8733	High Similarity	NPC477958
0.8732	High Similarity	NPC312881
0.8731	High Similarity	NPC221798
0.8725	High Similarity	NPC475790
0.8725	High Similarity	NPC35567
0.8725	High Similarity	NPC473996
0.8725	High Similarity	NPC243171
0.8725	High Similarity	NPC171651
0.8723	High Similarity	NPC155963
0.8716	High Similarity	NPC472421
0.8707	High Similarity	NPC98809
0.8707	High Similarity	NPC476394
0.8707	High Similarity	NPC10097
0.8699	High Similarity	NPC316769
0.8696	High Similarity	NPC104854
0.869	High Similarity	NPC18886
0.8675	High Similarity	NPC471787
0.8671	High Similarity	NPC80098
0.8671	High Similarity	NPC287286
0.8667	High Similarity	NPC165556
0.8667	High Similarity	NPC469405
0.8667	High Similarity	NPC293286
0.8662	High Similarity	NPC279573
0.8662	High Similarity	NPC211110
0.8658	High Similarity	NPC472580
0.8658	High Similarity	NPC472636
0.8658	High Similarity	NPC262039
0.8658	High Similarity	NPC278476
0.8658	High Similarity	NPC319910
0.8658	High Similarity	NPC474023
0.8658	High Similarity	NPC474021
0.8658	High Similarity	NPC254412
0.8658	High Similarity	NPC262038
0.8652	High Similarity	NPC294470
0.8652	High Similarity	NPC38099
0.8652	High Similarity	NPC26954
0.8649	High Similarity	NPC89442
0.8649	High Similarity	NPC139966
0.8649	High Similarity	NPC307052
0.8649	High Similarity	NPC472628
0.8643	High Similarity	NPC311339
0.8639	High Similarity	NPC202494
0.8639	High Similarity	NPC472627
0.8639	High Similarity	NPC472969
0.863	High Similarity	NPC291153
0.863	High Similarity	NPC124780
0.863	High Similarity	NPC87486
0.863	High Similarity	NPC294365
0.8623	High Similarity	NPC282230
0.8623	High Similarity	NPC183348
0.8613	High Similarity	NPC2596
0.8609	High Similarity	NPC108937
0.8609	High Similarity	NPC217706
0.8609	High Similarity	NPC470681
0.8609	High Similarity	NPC259710
0.8609	High Similarity	NPC304207
0.8609	High Similarity	NPC477530
0.8609	High Similarity	NPC207809
0.8609	High Similarity	NPC48579
0.8609	High Similarity	NPC279218
0.8603	High Similarity	NPC475236
0.86	High Similarity	NPC216035
0.86	High Similarity	NPC56232
0.86	High Similarity	NPC150123
0.86	High Similarity	NPC10807
0.86	High Similarity	NPC31627
0.86	High Similarity	NPC477957
0.86	High Similarity	NPC217149
0.86	High Similarity	NPC285623
0.86	High Similarity	NPC327269
0.86	High Similarity	NPC138288
0.86	High Similarity	NPC244583
0.86	High Similarity	NPC161881
0.86	High Similarity	NPC476238
0.8593	High Similarity	NPC184219
0.8592	High Similarity	NPC471069
0.8592	High Similarity	NPC281014
0.8592	High Similarity	NPC184861
0.8592	High Similarity	NPC225106
0.8592	High Similarity	NPC232246
0.8592	High Similarity	NPC294456
0.8592	High Similarity	NPC212124
0.8592	High Similarity	NPC471068
0.8592	High Similarity	NPC153818
0.8591	High Similarity	NPC470908
0.8591	High Similarity	NPC140133
0.8591	High Similarity	NPC105136
0.8582	High Similarity	NPC472525
0.8582	High Similarity	NPC291189
0.8582	High Similarity	NPC69403
0.8582	High Similarity	NPC476018
0.8582	High Similarity	NPC475029
0.8571	High Similarity	NPC14822
0.8571	High Similarity	NPC92589
0.8571	High Similarity	NPC469700
0.8571	High Similarity	NPC349525
0.8571	High Similarity	NPC97812
0.8571	High Similarity	NPC472629
0.8562	High Similarity	NPC469683
0.8561	High Similarity	NPC196979
0.8561	High Similarity	NPC470977
0.8561	High Similarity	NPC470976
0.8561	High Similarity	NPC15083
0.8553	High Similarity	NPC129053
0.8553	High Similarity	NPC321372
0.8553	High Similarity	NPC469936
0.8553	High Similarity	NPC20530
0.8553	High Similarity	NPC474738
0.8553	High Similarity	NPC474609
0.8553	High Similarity	NPC215917
0.8553	High Similarity	NPC78554
0.8553	High Similarity	NPC78492
0.8553	High Similarity	NPC10754
0.8553	High Similarity	NPC109967
0.8553	High Similarity	NPC475797
0.8553	High Similarity	NPC208152
0.8551	High Similarity	NPC473019
0.8551	High Similarity	NPC170546
0.8551	High Similarity	NPC66246
0.8551	High Similarity	NPC939
0.8543	High Similarity	NPC248793
0.8543	High Similarity	NPC180301
0.8542	High Similarity	NPC64664
0.8542	High Similarity	NPC79908
0.8533	High Similarity	NPC70016
0.8533	High Similarity	NPC215921
0.8533	High Similarity	NPC209846
0.8533	High Similarity	NPC328740
0.8533	High Similarity	NPC471675
0.8533	High Similarity	NPC477897
0.8533	High Similarity	NPC289774
0.8531	High Similarity	NPC471072
0.8531	High Similarity	NPC471070
0.8531	High Similarity	NPC471071
0.8523	High Similarity	NPC473091
0.8523	High Similarity	NPC164299
0.8521	High Similarity	NPC78746
0.8521	High Similarity	NPC475111
0.8521	High Similarity	NPC188380
0.8521	High Similarity	NPC224543
0.8514	High Similarity	NPC51070
0.8514	High Similarity	NPC222298
0.8514	High Similarity	NPC285748
0.8511	High Similarity	NPC224475
0.8511	High Similarity	NPC34456
0.8511	High Similarity	NPC50896
0.8511	High Similarity	NPC213173
0.8511	High Similarity	NPC62366
0.8511	High Similarity	NPC180716
0.8511	High Similarity	NPC326600
0.8511	High Similarity	NPC204353
0.8506	High Similarity	NPC239270
0.8506	High Similarity	NPC303210

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 NPC184053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	828
0.2-0.3	1632
0.3-0.4	2397
0.4-0.5	2024
0.5-0.6	1155
0.6-0.7	607
0.7-0.8	227
0.8-0.85	10
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9007	High Similarity	NPD4628	Phase 3
0.8803	High Similarity	NPD7421	Clinical (unspecified phase)
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD6801	Discontinued
0.8467	Intermediate Similarity	NPD4380	Phase 2
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD6799	Approved
0.8301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8138	Intermediate Similarity	NPD2799	Discontinued
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1934	Approved
0.8105	Intermediate Similarity	NPD6599	Discontinued
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD6798	Discontinued
0.8095	Intermediate Similarity	NPD1549	Phase 2
0.8082	Intermediate Similarity	NPD2935	Discontinued
0.8074	Intermediate Similarity	NPD9545	Approved
0.8056	Intermediate Similarity	NPD6355	Discontinued
0.8027	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7033	Discontinued
0.7973	Intermediate Similarity	NPD2424	Discontinued
0.7972	Intermediate Similarity	NPD2313	Discontinued
0.7959	Intermediate Similarity	NPD2796	Approved
0.7949	Intermediate Similarity	NPD8455	Phase 2
0.7931	Intermediate Similarity	NPD5124	Phase 1
0.7931	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7458	Discontinued
0.7908	Intermediate Similarity	NPD5403	Approved
0.7905	Intermediate Similarity	NPD6002	Phase 3
0.7905	Intermediate Similarity	NPD6005	Phase 3
0.7905	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6004	Phase 3
0.7905	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7867	Intermediate Similarity	NPD3750	Approved
0.7848	Intermediate Similarity	NPD7768	Phase 2
0.7843	Intermediate Similarity	NPD5049	Phase 3
0.784	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6166	Phase 2
0.784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3887	Approved
0.7815	Intermediate Similarity	NPD2354	Approved
0.7806	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3226	Approved
0.7793	Intermediate Similarity	NPD6233	Phase 2
0.7792	Intermediate Similarity	NPD920	Approved
0.7786	Intermediate Similarity	NPD1608	Approved
0.7786	Intermediate Similarity	NPD9717	Approved
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD5402	Approved
0.7785	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5401	Approved
0.777	Intermediate Similarity	NPD4308	Phase 3
0.777	Intermediate Similarity	NPD1510	Phase 2
0.7758	Intermediate Similarity	NPD7074	Phase 3
0.7748	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3818	Discontinued
0.774	Intermediate Similarity	NPD1240	Approved
0.774	Intermediate Similarity	NPD4060	Phase 1
0.7736	Intermediate Similarity	NPD3882	Suspended
0.7733	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2801	Approved
0.7718	Intermediate Similarity	NPD1551	Phase 2
0.7712	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3823	Discontinued
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7703	Intermediate Similarity	NPD7097	Phase 1
0.7702	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD7054	Approved
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7687	Intermediate Similarity	NPD447	Suspended
0.7682	Intermediate Similarity	NPD1243	Approved
0.7682	Intermediate Similarity	NPD1652	Phase 2
0.7671	Intermediate Similarity	NPD4062	Phase 3
0.7662	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1607	Approved
0.7632	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7003	Approved
0.7622	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD1203	Approved
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6273	Approved
0.761	Intermediate Similarity	NPD1465	Phase 2
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3764	Approved
0.7603	Intermediate Similarity	NPD3268	Approved
0.76	Intermediate Similarity	NPD4476	Approved
0.76	Intermediate Similarity	NPD4477	Approved
0.7597	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1091	Approved
0.7589	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6190	Approved
0.7578	Intermediate Similarity	NPD3749	Approved
0.7574	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD8312	Approved
0.7574	Intermediate Similarity	NPD1241	Discontinued
0.7572	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1778	Approved
0.7571	Intermediate Similarity	NPD17	Approved
0.7566	Intermediate Similarity	NPD2800	Approved
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7552	Intermediate Similarity	NPD8651	Approved
0.755	Intermediate Similarity	NPD2353	Approved
0.755	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD6959	Discontinued
0.7544	Intermediate Similarity	NPD8434	Phase 2
0.7531	Intermediate Similarity	NPD919	Approved
0.7518	Intermediate Similarity	NPD3496	Discontinued
0.7517	Intermediate Similarity	NPD9494	Approved
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.747	Intermediate Similarity	NPD7473	Discontinued
0.7465	Intermediate Similarity	NPD422	Phase 1
0.7463	Intermediate Similarity	NPD2684	Approved
0.7456	Intermediate Similarity	NPD7685	Pre-registration
0.745	Intermediate Similarity	NPD1933	Approved
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7448	Intermediate Similarity	NPD5647	Approved
0.7447	Intermediate Similarity	NPD4626	Approved
0.7439	Intermediate Similarity	NPD8127	Discontinued
0.7434	Intermediate Similarity	NPD5763	Approved
0.7434	Intermediate Similarity	NPD5762	Approved
0.7431	Intermediate Similarity	NPD3225	Approved
0.7429	Intermediate Similarity	NPD1894	Discontinued
0.7425	Intermediate Similarity	NPD7177	Discontinued
0.7419	Intermediate Similarity	NPD7440	Discontinued
0.7415	Intermediate Similarity	NPD7095	Approved
0.7413	Intermediate Similarity	NPD3972	Approved
0.7413	Intermediate Similarity	NPD1481	Phase 2
0.7405	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD6653	Approved
0.7388	Intermediate Similarity	NPD1358	Approved
0.7386	Intermediate Similarity	NPD4534	Discontinued
0.7384	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1613	Approved
0.7383	Intermediate Similarity	NPD3140	Approved
0.7383	Intermediate Similarity	NPD3142	Approved
0.7383	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5691	Approved
0.7375	Intermediate Similarity	NPD6385	Approved
0.7375	Intermediate Similarity	NPD6386	Approved
0.7372	Intermediate Similarity	NPD7843	Approved
0.7365	Intermediate Similarity	NPD411	Approved
0.7365	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2309	Approved
0.7351	Intermediate Similarity	NPD4538	Approved
0.7351	Intermediate Similarity	NPD4536	Approved
0.7351	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1535	Discovery
0.7342	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7157	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD4340	Discontinued
0.7329	Intermediate Similarity	NPD2798	Approved
0.7329	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4662	Approved
0.7325	Intermediate Similarity	NPD4661	Approved
0.7322	Intermediate Similarity	NPD7583	Approved
0.7321	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3751	Discontinued
0.731	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD5058	Phase 3
0.7308	Intermediate Similarity	NPD6666	Approved
0.7308	Intermediate Similarity	NPD6667	Approved
0.7305	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4110	Phase 3
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7286	Intermediate Similarity	NPD9493	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