NPASS Compound

Structure

NPC254233 OpenBabel07101718202D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 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 -3.4641 -0.2679 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 -0.0000 -2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7321 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 -1.7321 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 0.0000 1.0000 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 2.7321 -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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2321 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2321 -0.8660 0.0000 C 0 0 0 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 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7321 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2321 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 5 29 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 24 3 1 6 0 0 0 25 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.26
Volume:	446.056
LogP:	4.62
LogD:	3.681
LogS:	-5.083
# Rotatable Bonds:	8
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	3.854
Fsp3:	0.68
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:	-5.209
MDCK Permeability:	3.108813689323142e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.157
30% Bioavailability (F30%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	93.65143585205078%
Volume Distribution (VD):	0.499
Pgp-substrate:	3.70220685005188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.367
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.77
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.536
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	3.534
Half-life (T1/2):	0.722

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.619
Carcinogencity:	0.16
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.139

Download Data

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

Natural Product: NPC254233

Natural Product ID:	NPC254233
*Common Name:**	Abiesadine J
IUPAC Name:	4-[[(1R,4aS,10aR)-7-(2-methoxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methoxy]-4-oxobutanoic acid
Synonyms:
Standard InCHIKey:	OSBRSVNOFXCOHR-KSNOWIBYSA-N
Standard InCHI:	InChI=1S/C25H36O5/c1-23(2,29-5)18-8-9-19-17(15-18)7-10-20-24(3,13-6-14-25(19,20)4)16-30-22(28)12-11-21(26)27/h8-9,15,20H,6-7,10-14,16H2,1-5H3,(H,26,27)/t20-,24-,25+/m0/s1
SMILES:	COC(c1ccc2c(c1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)COC(=O)CCC(=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL592464
PubChem CID:	46230077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[572709]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[572709]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[572709]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[572709]

☑ 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 NPC254233 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	211
0.1-0.2	974
0.2-0.3	1992
0.3-0.4	5195
0.4-0.5	11387
0.5-0.6	16624
0.6-0.7	5575
0.7-0.8	690
0.8-0.85	29
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC242764
0.964	High Similarity	NPC105141
0.9381	High Similarity	NPC45794
0.9316	High Similarity	NPC307139
0.9244	High Similarity	NPC5486
0.9115	High Similarity	NPC221275
0.9	High Similarity	NPC21929
0.8992	High Similarity	NPC77691
0.8908	High Similarity	NPC182333
0.8908	High Similarity	NPC273336
0.8699	High Similarity	NPC115797
0.8699	High Similarity	NPC51448
0.8632	High Similarity	NPC212891
0.8596	High Similarity	NPC95126
0.8596	High Similarity	NPC475002
0.8468	Intermediate Similarity	NPC253681
0.8387	Intermediate Similarity	NPC9180
0.8387	Intermediate Similarity	NPC100402
0.832	Intermediate Similarity	NPC169913
0.8304	Intermediate Similarity	NPC19856
0.8264	Intermediate Similarity	NPC202015
0.8246	Intermediate Similarity	NPC94751
0.8246	Intermediate Similarity	NPC142326
0.824	Intermediate Similarity	NPC275576
0.824	Intermediate Similarity	NPC470765
0.8211	Intermediate Similarity	NPC293831
0.8211	Intermediate Similarity	NPC369
0.8205	Intermediate Similarity	NPC471188
0.8175	Intermediate Similarity	NPC470753
0.8175	Intermediate Similarity	NPC473220
0.812	Intermediate Similarity	NPC133308
0.8103	Intermediate Similarity	NPC475006
0.808	Intermediate Similarity	NPC85511
0.8049	Intermediate Similarity	NPC183339
0.8049	Intermediate Similarity	NPC133389
0.8049	Intermediate Similarity	NPC234337
0.8034	Intermediate Similarity	NPC273837
0.8017	Intermediate Similarity	NPC27252
0.8017	Intermediate Similarity	NPC472979
0.8016	Intermediate Similarity	NPC265413
0.8016	Intermediate Similarity	NPC10154
0.8016	Intermediate Similarity	NPC295664
0.8015	Intermediate Similarity	NPC329913
0.8	Intermediate Similarity	NPC471186
0.7965	Intermediate Similarity	NPC225079
0.7965	Intermediate Similarity	NPC469481
0.7965	Intermediate Similarity	NPC136810
0.7965	Intermediate Similarity	NPC133809
0.7965	Intermediate Similarity	NPC128248
0.7953	Intermediate Similarity	NPC137416
0.7937	Intermediate Similarity	NPC140118
0.7937	Intermediate Similarity	NPC328107
0.7937	Intermediate Similarity	NPC12881
0.792	Intermediate Similarity	NPC269923
0.792	Intermediate Similarity	NPC167323
0.7917	Intermediate Similarity	NPC153053
0.7899	Intermediate Similarity	NPC270699
0.7899	Intermediate Similarity	NPC82899
0.7879	Intermediate Similarity	NPC126516
0.7879	Intermediate Similarity	NPC203486
0.7879	Intermediate Similarity	NPC48929
0.7876	Intermediate Similarity	NPC221825
0.7874	Intermediate Similarity	NPC474532
0.7869	Intermediate Similarity	NPC470820
0.7863	Intermediate Similarity	NPC472980
0.7851	Intermediate Similarity	NPC473869
0.7846	Intermediate Similarity	NPC147561
0.7846	Intermediate Similarity	NPC131684
0.7845	Intermediate Similarity	NPC243601
0.782	Intermediate Similarity	NPC477893
0.782	Intermediate Similarity	NPC471864
0.782	Intermediate Similarity	NPC212207
0.782	Intermediate Similarity	NPC477896
0.7815	Intermediate Similarity	NPC305912
0.7815	Intermediate Similarity	NPC1082
0.7797	Intermediate Similarity	NPC149455
0.7797	Intermediate Similarity	NPC64642
0.7797	Intermediate Similarity	NPC472982
0.7795	Intermediate Similarity	NPC51079
0.7787	Intermediate Similarity	NPC9274
0.7786	Intermediate Similarity	NPC249425
0.7778	Intermediate Similarity	NPC473889
0.776	Intermediate Similarity	NPC238861
0.776	Intermediate Similarity	NPC77000
0.7759	Intermediate Similarity	NPC472222
0.7759	Intermediate Similarity	NPC472221
0.775	Intermediate Similarity	NPC321852
0.7731	Intermediate Similarity	NPC251854
0.7731	Intermediate Similarity	NPC93084
0.7731	Intermediate Similarity	NPC196246
0.7731	Intermediate Similarity	NPC214067
0.7727	Intermediate Similarity	NPC258073
0.7721	Intermediate Similarity	NPC171207
0.7721	Intermediate Similarity	NPC275592
0.7721	Intermediate Similarity	NPC97667
0.7721	Intermediate Similarity	NPC100913
0.7721	Intermediate Similarity	NPC90614
0.7717	Intermediate Similarity	NPC478058
0.7717	Intermediate Similarity	NPC473870
0.7717	Intermediate Similarity	NPC473871
0.771	Intermediate Similarity	NPC471832
0.7705	Intermediate Similarity	NPC474095
0.7704	Intermediate Similarity	NPC262324
0.7699	Intermediate Similarity	NPC226041
0.7681	Intermediate Similarity	NPC477894
0.768	Intermediate Similarity	NPC204784
0.7674	Intermediate Similarity	NPC470816
0.7667	Intermediate Similarity	NPC260818
0.7664	Intermediate Similarity	NPC87448
0.7664	Intermediate Similarity	NPC27377
0.7664	Intermediate Similarity	NPC97947
0.7664	Intermediate Similarity	NPC471862
0.7664	Intermediate Similarity	NPC16912
0.7664	Intermediate Similarity	NPC118080
0.7664	Intermediate Similarity	NPC41481
0.7664	Intermediate Similarity	NPC472576
0.7664	Intermediate Similarity	NPC291599
0.7661	Intermediate Similarity	NPC84129
0.7661	Intermediate Similarity	NPC152812
0.7656	Intermediate Similarity	NPC318067
0.7652	Intermediate Similarity	NPC470278
0.7652	Intermediate Similarity	NPC245927
0.7652	Intermediate Similarity	NPC72915
0.7647	Intermediate Similarity	NPC17417
0.7647	Intermediate Similarity	NPC10251
0.7634	Intermediate Similarity	NPC225103
0.763	Intermediate Similarity	NPC472372
0.763	Intermediate Similarity	NPC472551
0.763	Intermediate Similarity	NPC309056
0.763	Intermediate Similarity	NPC472545
0.763	Intermediate Similarity	NPC472374
0.7623	Intermediate Similarity	NPC307651
0.7619	Intermediate Similarity	NPC473243
0.7619	Intermediate Similarity	NPC260832
0.7619	Intermediate Similarity	NPC135467
0.7615	Intermediate Similarity	NPC51292
0.7612	Intermediate Similarity	NPC474608
0.7603	Intermediate Similarity	NPC471189
0.76	Intermediate Similarity	NPC473860
0.7594	Intermediate Similarity	NPC209851
0.7594	Intermediate Similarity	NPC472394
0.7594	Intermediate Similarity	NPC471880
0.7591	Intermediate Similarity	NPC472547
0.7591	Intermediate Similarity	NPC79921
0.7591	Intermediate Similarity	NPC265335
0.7581	Intermediate Similarity	NPC472862
0.7578	Intermediate Similarity	NPC472703
0.7578	Intermediate Similarity	NPC12016
0.7578	Intermediate Similarity	NPC121168
0.7576	Intermediate Similarity	NPC472388
0.7576	Intermediate Similarity	NPC473443
0.7574	Intermediate Similarity	NPC39549
0.7574	Intermediate Similarity	NPC243893
0.7571	Intermediate Similarity	NPC127857
0.7568	Intermediate Similarity	NPC220596
0.7563	Intermediate Similarity	NPC56493
0.7561	Intermediate Similarity	NPC186933
0.7559	Intermediate Similarity	NPC164852
0.7559	Intermediate Similarity	NPC50872
0.7556	Intermediate Similarity	NPC27394
0.7556	Intermediate Similarity	NPC195647
0.7556	Intermediate Similarity	NPC17877
0.7556	Intermediate Similarity	NPC66761
0.7556	Intermediate Similarity	NPC194970
0.7556	Intermediate Similarity	NPC472577
0.7556	Intermediate Similarity	NPC291638
0.7554	Intermediate Similarity	NPC477468
0.7554	Intermediate Similarity	NPC163087
0.7545	Intermediate Similarity	NPC220893
0.7541	Intermediate Similarity	NPC128368
0.7541	Intermediate Similarity	NPC265002
0.754	Intermediate Similarity	NPC42657
0.7538	Intermediate Similarity	NPC475933
0.7538	Intermediate Similarity	NPC476970
0.7538	Intermediate Similarity	NPC470158
0.7536	Intermediate Similarity	NPC224491
0.7519	Intermediate Similarity	NPC470815
0.7519	Intermediate Similarity	NPC475102
0.7519	Intermediate Similarity	NPC472704
0.7519	Intermediate Similarity	NPC469742
0.7519	Intermediate Similarity	NPC472373
0.75	Intermediate Similarity	NPC472569
0.75	Intermediate Similarity	NPC472570
0.75	Intermediate Similarity	NPC469511
0.75	Intermediate Similarity	NPC249340
0.75	Intermediate Similarity	NPC279463
0.75	Intermediate Similarity	NPC25768
0.75	Intermediate Similarity	NPC173569
0.75	Intermediate Similarity	NPC95810
0.75	Intermediate Similarity	NPC162935
0.75	Intermediate Similarity	NPC477874
0.75	Intermediate Similarity	NPC188865
0.75	Intermediate Similarity	NPC70716
0.75	Intermediate Similarity	NPC11685
0.75	Intermediate Similarity	NPC472573
0.75	Intermediate Similarity	NPC163719
0.75	Intermediate Similarity	NPC125106
0.75	Intermediate Similarity	NPC241951
0.75	Intermediate Similarity	NPC85493
0.75	Intermediate Similarity	NPC475759

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 NPC254233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	727
0.2-0.3	1216
0.3-0.4	2605
0.4-0.5	2440
0.5-0.6	1487
0.6-0.7	450
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8547	High Similarity	NPD4198	Discontinued
0.8125	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7741	Discontinued
0.7851	Intermediate Similarity	NPD5951	Approved
0.7846	Intermediate Similarity	NPD7008	Discontinued
0.776	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5736	Approved
0.7647	Intermediate Similarity	NPD2182	Approved
0.7619	Intermediate Similarity	NPD5126	Approved
0.7619	Intermediate Similarity	NPD5125	Phase 3
0.7561	Intermediate Similarity	NPD2629	Approved
0.748	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD6663	Approved
0.7447	Intermediate Similarity	NPD7236	Approved
0.7407	Intermediate Similarity	NPD4140	Approved
0.7377	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7097	Phase 1
0.7355	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6010	Discontinued
0.7333	Intermediate Similarity	NPD7961	Discontinued
0.7328	Intermediate Similarity	NPD1283	Approved
0.7313	Intermediate Similarity	NPD7095	Approved
0.7311	Intermediate Similarity	NPD164	Approved
0.731	Intermediate Similarity	NPD7239	Suspended
0.7279	Intermediate Similarity	NPD2979	Phase 3
0.7259	Intermediate Similarity	NPD7985	Registered
0.7258	Intermediate Similarity	NPD6858	Approved
0.7258	Intermediate Similarity	NPD7094	Approved
0.7218	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6085	Phase 2
0.7217	Intermediate Similarity	NPD6049	Phase 2
0.7217	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8032	Phase 2
0.7206	Intermediate Similarity	NPD7715	Approved
0.7206	Intermediate Similarity	NPD7714	Approved
0.7194	Intermediate Similarity	NPD7305	Phase 1
0.7193	Intermediate Similarity	NPD1088	Approved
0.7183	Intermediate Similarity	NPD8166	Discontinued
0.7183	Intermediate Similarity	NPD7003	Approved
0.7167	Intermediate Similarity	NPD5909	Discontinued
0.7155	Intermediate Similarity	NPD1989	Approved
0.7154	Intermediate Similarity	NPD5235	Approved
0.7154	Intermediate Similarity	NPD5236	Approved
0.7154	Intermediate Similarity	NPD5240	Approved
0.7154	Intermediate Similarity	NPD5239	Approved
0.7154	Intermediate Similarity	NPD5237	Approved
0.7132	Intermediate Similarity	NPD5585	Approved
0.7132	Intermediate Similarity	NPD5691	Approved
0.7119	Intermediate Similarity	NPD2066	Phase 3
0.7099	Intermediate Similarity	NPD6287	Discontinued
0.7099	Intermediate Similarity	NPD1281	Approved
0.7092	Intermediate Similarity	NPD2346	Discontinued
0.7092	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6647	Phase 2
0.7077	Intermediate Similarity	NPD4626	Approved
0.7077	Intermediate Similarity	NPD3019	Approved
0.7069	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6685	Approved
0.7029	Intermediate Similarity	NPD4060	Phase 1
0.7023	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1090	Approved
0.7018	Intermediate Similarity	NPD1086	Approved
0.7018	Intermediate Similarity	NPD1089	Approved
0.7007	Intermediate Similarity	NPD3764	Approved
0.6992	Remote Similarity	NPD5327	Phase 3
0.6984	Remote Similarity	NPD7635	Approved
0.697	Remote Similarity	NPD4807	Approved
0.697	Remote Similarity	NPD5618	Discontinued
0.697	Remote Similarity	NPD4806	Approved
0.697	Remote Similarity	NPD1611	Approved
0.6963	Remote Similarity	NPD4624	Approved
0.696	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.696	Remote Similarity	NPD2201	Approved
0.6953	Remote Similarity	NPD3317	Approved
0.6947	Remote Similarity	NPD2932	Approved
0.6947	Remote Similarity	NPD3095	Discontinued
0.6947	Remote Similarity	NPD5305	Approved
0.6947	Remote Similarity	NPD5306	Approved
0.6947	Remote Similarity	NPD1778	Approved
0.6942	Remote Similarity	NPD1930	Approved
0.6942	Remote Similarity	NPD1929	Approved
0.6942	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6273	Approved
0.693	Remote Similarity	NPD800	Approved
0.6929	Remote Similarity	NPD6353	Approved
0.6923	Remote Similarity	NPD1693	Approved
0.6923	Remote Similarity	NPD3091	Approved
0.6913	Remote Similarity	NPD7458	Discontinued
0.6905	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2438	Suspended
0.6901	Remote Similarity	NPD2531	Phase 2
0.6894	Remote Similarity	NPD3026	Approved
0.6894	Remote Similarity	NPD3023	Approved
0.688	Remote Similarity	NPD2067	Discontinued
0.687	Remote Similarity	NPD1651	Approved
0.687	Remote Similarity	NPD3024	Approved
0.687	Remote Similarity	NPD3025	Approved
0.6866	Remote Similarity	NPD4359	Approved
0.6857	Remote Similarity	NPD5735	Approved
0.6857	Remote Similarity	NPD6355	Discontinued
0.6853	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5762	Approved
0.6853	Remote Similarity	NPD5763	Approved
0.685	Remote Similarity	NPD5535	Approved
0.6846	Remote Similarity	NPD7644	Approved
0.6846	Remote Similarity	NPD6065	Approved
0.6838	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7798	Approved
0.6833	Remote Similarity	NPD1238	Approved
0.6828	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4199	Phase 3
0.6818	Remote Similarity	NPD7725	Approved
0.681	Remote Similarity	NPD1239	Approved
0.6807	Remote Similarity	NPD1565	Approved
0.6807	Remote Similarity	NPD1564	Approved
0.6807	Remote Similarity	NPD1566	Phase 3
0.6803	Remote Similarity	NPD5765	Approved
0.68	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3226	Approved
0.68	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4477	Approved
0.6783	Remote Similarity	NPD4476	Approved
0.6769	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD4135	Approved
0.6767	Remote Similarity	NPD4106	Approved
0.6767	Remote Similarity	NPD4136	Approved
0.6767	Remote Similarity	NPD3847	Discontinued
0.6765	Remote Similarity	NPD2797	Approved
0.6765	Remote Similarity	NPD3094	Phase 2
0.6763	Remote Similarity	NPD6798	Discontinued
0.6763	Remote Similarity	NPD2313	Discontinued
0.6757	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD1087	Approved
0.6753	Remote Similarity	NPD7057	Phase 3
0.6753	Remote Similarity	NPD7058	Phase 2
0.675	Remote Similarity	NPD5926	Approved
0.6748	Remote Similarity	NPD3046	Approved
0.6748	Remote Similarity	NPD3047	Approved
0.6748	Remote Similarity	NPD3048	Approved
0.6744	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD3672	Approved
0.6724	Remote Similarity	NPD3673	Approved
0.6721	Remote Similarity	NPD1932	Approved
0.672	Remote Similarity	NPD2342	Discontinued
0.6718	Remote Similarity	NPD7610	Discontinued
0.6716	Remote Similarity	NPD3092	Approved
0.6716	Remote Similarity	NPD4480	Approved
0.6714	Remote Similarity	NPD6233	Phase 2
0.6713	Remote Similarity	NPD2799	Discontinued
0.6712	Remote Similarity	NPD4628	Phase 3
0.6712	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4110	Phase 3
0.6694	Remote Similarity	NPD5048	Discontinued
0.6692	Remote Similarity	NPD7157	Approved
0.6692	Remote Similarity	NPD4059	Approved
0.6691	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6696	Suspended
0.6691	Remote Similarity	NPD5667	Approved
0.669	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD7250	Approved
0.6667	Remote Similarity	NPD6637	Approved
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD4479	Discontinued
0.6667	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7249	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6644	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3268	Approved
0.6643	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD41	Approved
0.6643	Remote Similarity	NPD5886	Approved
0.6642	Remote Similarity	NPD3496	Discontinued
0.6642	Remote Similarity	NPD3898	Approved
0.6642	Remote Similarity	NPD6362	Approved
0.6642	Remote Similarity	NPD3895	Approved
0.6642	Remote Similarity	NPD3896	Approved
0.6642	Remote Similarity	NPD3897	Approved
0.6641	Remote Similarity	NPD6912	Phase 3
0.6641	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7340	Approved
0.6638	Remote Similarity	NPD5346	Phase 2
0.6638	Remote Similarity	NPD5347	Phase 2
0.6621	Remote Similarity	NPD6002	Phase 3
0.6621	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6005	Phase 3
0.6621	Remote Similarity	NPD6003	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