NPASS Compound

Structure

NPC212891 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 2.6980 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 -2.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 4.3301 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 1 0 0 0 16 19 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	2.925
LogD:	2.187
LogS:	-3.453
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	3.924
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.354
MDCK Permeability:	1.677456748438999e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	87.46776580810547%
Volume Distribution (VD):	0.431
Pgp-substrate:	14.790979385375977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.809
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.183
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	1.653
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.312
Carcinogencity:	0.041
Eye Corrosion:	0.006
Eye Irritation:	0.082
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC212891

Natural Product ID:	NPC212891
*Common Name:**	Majusanic Acid B
IUPAC Name:	(1S,4aS,10aR)-7-[(2R)-1,2-dihydroxypropan-2-yl]-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	AKLQGVMKOBBNLW-LMCOJAPRSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-18-9-4-10-19(2,17(22)23)16(18)8-5-13-11-14(6-7-15(13)18)20(3,24)12-21/h6-7,11,16,21,24H,4-5,8-10,12H2,1-3H3,(H,22,23)/t16-,18-,19+,20+/m1/s1
SMILES:	OC[C@@](c1ccc2c(c1)CC[C@@H]1[C@]2(C)CCC[C@]1(C)C(=O)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431479
PubChem CID:	73355402
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
NPO14738	Illicium majus	Species	Schisandraceae	Eukaryota	Roots	n.a.	n.a.	PMID[24070022]
NPO14738	Illicium majus	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14738	Illicium majus	Species	Schisandraceae	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
IC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	=	138.7	uM/ml	PMID[508873]
NPT2	Others	Unspecified		Selectivity Index	=	6.2	n.a.	PMID[508873]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	22200000.0	nM	PMID[508873]

☑ 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 NPC212891 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	194
0.1-0.2	877
0.2-0.3	1946
0.3-0.4	5178
0.4-0.5	11226
0.5-0.6	17228
0.6-0.7	5216
0.7-0.8	757
0.8-0.85	44
0.85-0.9	20
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC95126
0.9444	High Similarity	NPC475002
0.9182	High Similarity	NPC471188
0.9138	High Similarity	NPC369
0.9138	High Similarity	NPC293831
0.9107	High Similarity	NPC221275
0.9074	High Similarity	NPC142326
0.9074	High Similarity	NPC94751
0.9035	High Similarity	NPC45794
0.8966	High Similarity	NPC183339
0.8966	High Similarity	NPC133389
0.8966	High Similarity	NPC234337
0.8947	High Similarity	NPC105141
0.8947	High Similarity	NPC242764
0.8807	High Similarity	NPC471186
0.8796	High Similarity	NPC19856
0.876	High Similarity	NPC253681
0.8667	High Similarity	NPC85511
0.8655	High Similarity	NPC269923
0.8655	High Similarity	NPC167323
0.8632	High Similarity	NPC254233
0.8611	High Similarity	NPC128248
0.8611	High Similarity	NPC133809
0.8611	High Similarity	NPC136810
0.8611	High Similarity	NPC225079
0.8584	High Similarity	NPC133308
0.8537	High Similarity	NPC51448
0.8537	High Similarity	NPC115797
0.8512	High Similarity	NPC77691
0.8482	Intermediate Similarity	NPC27252
0.8482	Intermediate Similarity	NPC472979
0.844	Intermediate Similarity	NPC469481
0.843	Intermediate Similarity	NPC273336
0.843	Intermediate Similarity	NPC182333
0.8349	Intermediate Similarity	NPC221825
0.8348	Intermediate Similarity	NPC471189
0.8319	Intermediate Similarity	NPC472980
0.8306	Intermediate Similarity	NPC5486
0.8304	Intermediate Similarity	NPC243601
0.8291	Intermediate Similarity	NPC186933
0.8264	Intermediate Similarity	NPC472981
0.825	Intermediate Similarity	NPC42657
0.8246	Intermediate Similarity	NPC149455
0.8246	Intermediate Similarity	NPC64642
0.8246	Intermediate Similarity	NPC472982
0.8197	Intermediate Similarity	NPC249340
0.8197	Intermediate Similarity	NPC162935
0.819	Intermediate Similarity	NPC66208
0.8165	Intermediate Similarity	NPC226041
0.8158	Intermediate Similarity	NPC21929
0.813	Intermediate Similarity	NPC121168
0.8115	Intermediate Similarity	NPC241001
0.8103	Intermediate Similarity	NPC265513
0.808	Intermediate Similarity	NPC275576
0.8067	Intermediate Similarity	NPC9274
0.8065	Intermediate Similarity	NPC307139
0.8065	Intermediate Similarity	NPC471187
0.8053	Intermediate Similarity	NPC472222
0.8053	Intermediate Similarity	NPC472221
0.8051	Intermediate Similarity	NPC471721
0.8051	Intermediate Similarity	NPC196673
0.8016	Intermediate Similarity	NPC169913
0.8	Intermediate Similarity	NPC158157
0.8	Intermediate Similarity	NPC181334
0.7984	Intermediate Similarity	NPC11250
0.7983	Intermediate Similarity	NPC93181
0.7969	Intermediate Similarity	NPC131684
0.7967	Intermediate Similarity	NPC164852
0.7966	Intermediate Similarity	NPC93287
0.7951	Intermediate Similarity	NPC202015
0.7949	Intermediate Similarity	NPC474057
0.7937	Intermediate Similarity	NPC100402
0.7937	Intermediate Similarity	NPC9180
0.7937	Intermediate Similarity	NPC137416
0.7937	Intermediate Similarity	NPC470765
0.7931	Intermediate Similarity	NPC318327
0.7931	Intermediate Similarity	NPC475006
0.792	Intermediate Similarity	NPC198014
0.7903	Intermediate Similarity	NPC253627
0.7895	Intermediate Similarity	NPC315794
0.7886	Intermediate Similarity	NPC470585
0.7886	Intermediate Similarity	NPC478121
0.7874	Intermediate Similarity	NPC470753
0.7874	Intermediate Similarity	NPC473220
0.787	Intermediate Similarity	NPC220596
0.7852	Intermediate Similarity	NPC3218
0.7851	Intermediate Similarity	NPC472862
0.7846	Intermediate Similarity	NPC313663
0.7833	Intermediate Similarity	NPC215419
0.7823	Intermediate Similarity	NPC259703
0.7823	Intermediate Similarity	NPC32322
0.7815	Intermediate Similarity	NPC470253
0.7805	Intermediate Similarity	NPC476645
0.7803	Intermediate Similarity	NPC477896
0.7803	Intermediate Similarity	NPC293454
0.7795	Intermediate Similarity	NPC137750
0.7795	Intermediate Similarity	NPC87985
0.7794	Intermediate Similarity	NPC272907
0.7794	Intermediate Similarity	NPC2681
0.7787	Intermediate Similarity	NPC323440
0.7787	Intermediate Similarity	NPC80605
0.7787	Intermediate Similarity	NPC222968
0.7778	Intermediate Similarity	NPC328107
0.7778	Intermediate Similarity	NPC12881
0.7778	Intermediate Similarity	NPC140118
0.7778	Intermediate Similarity	NPC473938
0.7768	Intermediate Similarity	NPC160548
0.7768	Intermediate Similarity	NPC210529
0.7768	Intermediate Similarity	NPC175852
0.7742	Intermediate Similarity	NPC190501
0.7742	Intermediate Similarity	NPC318552
0.7734	Intermediate Similarity	NPC171007
0.7734	Intermediate Similarity	NPC190849
0.7731	Intermediate Similarity	NPC280789
0.7731	Intermediate Similarity	NPC111108
0.7727	Intermediate Similarity	NPC475457
0.7727	Intermediate Similarity	NPC18982
0.7727	Intermediate Similarity	NPC475627
0.7727	Intermediate Similarity	NPC476282
0.7727	Intermediate Similarity	NPC475346
0.7727	Intermediate Similarity	NPC49742
0.7724	Intermediate Similarity	NPC328694
0.7719	Intermediate Similarity	NPC304873
0.7717	Intermediate Similarity	NPC295664
0.771	Intermediate Similarity	NPC291001
0.771	Intermediate Similarity	NPC243305
0.771	Intermediate Similarity	NPC476847
0.7705	Intermediate Similarity	NPC92
0.7705	Intermediate Similarity	NPC469663
0.7704	Intermediate Similarity	NPC275592
0.7704	Intermediate Similarity	NPC100913
0.7698	Intermediate Similarity	NPC108286
0.7698	Intermediate Similarity	NPC176208
0.7692	Intermediate Similarity	NPC249811
0.7687	Intermediate Similarity	NPC39549
0.7685	Intermediate Similarity	NPC1793
0.7681	Intermediate Similarity	NPC477207
0.7679	Intermediate Similarity	NPC324602
0.7674	Intermediate Similarity	NPC262936
0.7674	Intermediate Similarity	NPC30491
0.7672	Intermediate Similarity	NPC471133
0.7672	Intermediate Similarity	NPC105899
0.7669	Intermediate Similarity	NPC202225
0.7669	Intermediate Similarity	NPC471864
0.7669	Intermediate Similarity	NPC477893
0.7667	Intermediate Similarity	NPC306977
0.7667	Intermediate Similarity	NPC287055
0.7667	Intermediate Similarity	NPC242957
0.7667	Intermediate Similarity	NPC206414
0.7664	Intermediate Similarity	NPC91703
0.7661	Intermediate Similarity	NPC472708
0.7658	Intermediate Similarity	NPC172925
0.7656	Intermediate Similarity	NPC470816
0.7652	Intermediate Similarity	NPC255676
0.7652	Intermediate Similarity	NPC160382
0.7647	Intermediate Similarity	NPC27377
0.7647	Intermediate Similarity	NPC97947
0.7647	Intermediate Similarity	NPC87448
0.7647	Intermediate Similarity	NPC118080
0.7647	Intermediate Similarity	NPC41481
0.7647	Intermediate Similarity	NPC472576
0.7647	Intermediate Similarity	NPC291599
0.7636	Intermediate Similarity	NPC128645
0.7634	Intermediate Similarity	NPC72915
0.7632	Intermediate Similarity	NPC289117
0.7632	Intermediate Similarity	NPC264728
0.763	Intermediate Similarity	NPC477592
0.763	Intermediate Similarity	NPC471152
0.7626	Intermediate Similarity	NPC126707
0.7623	Intermediate Similarity	NPC35797
0.7623	Intermediate Similarity	NPC192948
0.7619	Intermediate Similarity	NPC154696
0.7615	Intermediate Similarity	NPC86670
0.7615	Intermediate Similarity	NPC274455
0.7615	Intermediate Similarity	NPC70940
0.7612	Intermediate Similarity	NPC472545
0.7612	Intermediate Similarity	NPC472551
0.7612	Intermediate Similarity	NPC279463
0.7612	Intermediate Similarity	NPC472804
0.7612	Intermediate Similarity	NPC472374
0.7612	Intermediate Similarity	NPC472372
0.7597	Intermediate Similarity	NPC71610
0.7597	Intermediate Similarity	NPC474106
0.7594	Intermediate Similarity	NPC126516
0.7594	Intermediate Similarity	NPC203486
0.7594	Intermediate Similarity	NPC48929
0.7591	Intermediate Similarity	NPC304110
0.7591	Intermediate Similarity	NPC27518
0.7586	Intermediate Similarity	NPC56168
0.7581	Intermediate Similarity	NPC318173
0.7578	Intermediate Similarity	NPC265413
0.7578	Intermediate Similarity	NPC10154
0.7578	Intermediate Similarity	NPC15127
0.7576	Intermediate Similarity	NPC471851
0.7576	Intermediate Similarity	NPC258073
0.7574	Intermediate Similarity	NPC97667
0.7574	Intermediate Similarity	NPC171207
0.7574	Intermediate Similarity	NPC90614
0.7574	Intermediate Similarity	NPC472547
0.7565	Intermediate Similarity	NPC25458

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 NPC212891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	694
0.2-0.3	1215
0.3-0.4	2567
0.4-0.5	2462
0.5-0.6	1511
0.6-0.7	449
0.7-0.8	69
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD5951	Approved
0.8448	Intermediate Similarity	NPD2629	Approved
0.8254	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD4198	Discontinued
0.8182	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD7008	Discontinued
0.7949	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7715	Approved
0.7846	Intermediate Similarity	NPD7714	Approved
0.7807	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1088	Approved
0.7768	Intermediate Similarity	NPD9495	Approved
0.775	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3019	Approved
0.771	Intermediate Similarity	NPD6663	Approved
0.7699	Intermediate Similarity	NPD2066	Phase 3
0.7674	Intermediate Similarity	NPD5736	Approved
0.7658	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1086	Approved
0.7615	Intermediate Similarity	NPD1089	Approved
0.7615	Intermediate Similarity	NPD1090	Approved
0.76	Intermediate Similarity	NPD5305	Approved
0.76	Intermediate Similarity	NPD2932	Approved
0.76	Intermediate Similarity	NPD5306	Approved
0.7523	Intermediate Similarity	NPD800	Approved
0.75	Intermediate Similarity	NPD1693	Approved
0.75	Intermediate Similarity	NPD1930	Approved
0.75	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1929	Approved
0.748	Intermediate Similarity	NPD4807	Approved
0.748	Intermediate Similarity	NPD4806	Approved
0.746	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7741	Discontinued
0.7434	Intermediate Similarity	NPD1989	Approved
0.7411	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD8166	Discontinued
0.7402	Intermediate Similarity	NPD3026	Approved
0.7402	Intermediate Similarity	NPD4106	Approved
0.7402	Intermediate Similarity	NPD4136	Approved
0.7402	Intermediate Similarity	NPD3023	Approved
0.7402	Intermediate Similarity	NPD4135	Approved
0.7387	Intermediate Similarity	NPD1239	Approved
0.7381	Intermediate Similarity	NPD3024	Approved
0.7381	Intermediate Similarity	NPD3025	Approved
0.7377	Intermediate Similarity	NPD6858	Approved
0.7377	Intermediate Similarity	NPD7094	Approved
0.7368	Intermediate Similarity	NPD1566	Phase 3
0.7368	Intermediate Similarity	NPD1564	Approved
0.7368	Intermediate Similarity	NPD1565	Approved
0.7345	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6049	Phase 2
0.7344	Intermediate Similarity	NPD3092	Approved
0.7339	Intermediate Similarity	NPD1087	Approved
0.7323	Intermediate Similarity	NPD4199	Phase 3
0.7323	Intermediate Similarity	NPD5126	Approved
0.7323	Intermediate Similarity	NPD5125	Phase 3
0.7317	Intermediate Similarity	NPD6010	Discontinued
0.7308	Intermediate Similarity	NPD1283	Approved
0.7302	Intermediate Similarity	NPD3091	Approved
0.7299	Intermediate Similarity	NPD7305	Phase 1
0.7288	Intermediate Similarity	NPD5909	Discontinued
0.7286	Intermediate Similarity	NPD7003	Approved
0.7252	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD4102	Approved
0.7244	Intermediate Similarity	NPD4105	Approved
0.7227	Intermediate Similarity	NPD5048	Discontinued
0.7203	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6647	Phase 2
0.72	Intermediate Similarity	NPD3317	Approved
0.7197	Intermediate Similarity	NPD6085	Phase 2
0.7197	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3095	Discontinued
0.7183	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD1237	Approved
0.7105	Intermediate Similarity	NPD1563	Approved
0.7094	Intermediate Similarity	NPD7798	Approved
0.709	Intermediate Similarity	NPD4620	Approved
0.709	Intermediate Similarity	NPD5203	Approved
0.709	Intermediate Similarity	NPD4617	Approved
0.709	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5201	Approved
0.7087	Intermediate Similarity	NPD7610	Discontinued
0.7077	Intermediate Similarity	NPD5618	Discontinued
0.7077	Intermediate Similarity	NPD1281	Approved
0.7073	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3495	Discontinued
0.7059	Intermediate Similarity	NPD7961	Discontinued
0.7055	Intermediate Similarity	NPD7239	Suspended
0.7054	Intermediate Similarity	NPD5346	Phase 2
0.7054	Intermediate Similarity	NPD7725	Approved
0.7054	Intermediate Similarity	NPD5347	Phase 2
0.7049	Intermediate Similarity	NPD2182	Approved
0.7042	Intermediate Similarity	NPD4628	Phase 3
0.7015	Intermediate Similarity	NPD5204	Approved
0.7007	Intermediate Similarity	NPD2979	Phase 3
0.7007	Intermediate Similarity	NPD4140	Approved
0.7007	Intermediate Similarity	NPD7458	Discontinued
0.7007	Intermediate Similarity	NPD5119	Approved
0.7007	Intermediate Similarity	NPD5121	Approved
0.7007	Intermediate Similarity	NPD5120	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6991	Remote Similarity	NPD3672	Approved
0.6991	Remote Similarity	NPD3673	Approved
0.6984	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1932	Approved
0.6972	Remote Similarity	NPD9491	Approved
0.697	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2342	Discontinued
0.696	Remote Similarity	NPD7635	Approved
0.6947	Remote Similarity	NPD6287	Discontinued
0.6944	Remote Similarity	NPD226	Approved
0.6934	Remote Similarity	NPD8032	Phase 2
0.6923	Remote Similarity	NPD4059	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6917	Remote Similarity	NPD5765	Approved
0.6912	Remote Similarity	NPD7095	Approved
0.6912	Remote Similarity	NPD6966	Discovery
0.6911	Remote Similarity	NPD2329	Discontinued
0.6899	Remote Similarity	NPD7009	Phase 2
0.6894	Remote Similarity	NPD4878	Approved
0.6892	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3661	Approved
0.6889	Remote Similarity	NPD3663	Approved
0.6889	Remote Similarity	NPD3662	Phase 3
0.6889	Remote Similarity	NPD3664	Approved
0.6885	Remote Similarity	NPD6685	Approved
0.6884	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD2438	Suspended
0.6875	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4793	Discontinued
0.687	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6798	Discontinued
0.6861	Remote Similarity	NPD4619	Approved
0.6861	Remote Similarity	NPD4621	Approved
0.6861	Remote Similarity	NPD3764	Approved
0.686	Remote Similarity	NPD164	Approved
0.6849	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1651	Approved
0.6842	Remote Similarity	NPD9256	Approved
0.6842	Remote Similarity	NPD9258	Approved
0.6835	Remote Similarity	NPD6355	Discontinued
0.6831	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3971	Phase 1
0.6818	Remote Similarity	NPD1201	Approved
0.681	Remote Similarity	NPD1202	Approved
0.6807	Remote Similarity	NPD3020	Approved
0.6794	Remote Similarity	NPD4626	Approved
0.6779	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2652	Approved
0.6772	Remote Similarity	NPD2650	Approved
0.6769	Remote Similarity	NPD4479	Discontinued
0.6769	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6311	Approved
0.6763	Remote Similarity	NPD6309	Approved
0.6763	Remote Similarity	NPD6310	Approved
0.6761	Remote Similarity	NPD4172	Approved
0.6761	Remote Similarity	NPD2531	Phase 2
0.6761	Remote Similarity	NPD4173	Approved
0.6744	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2628	Approved
0.6741	Remote Similarity	NPD2625	Approved
0.6741	Remote Similarity	NPD2627	Approved
0.6741	Remote Similarity	NPD1470	Approved
0.6741	Remote Similarity	NPD2159	Approved
0.6741	Remote Similarity	NPD2160	Approved
0.6741	Remote Similarity	NPD2626	Approved
0.6741	Remote Similarity	NPD2797	Approved
0.672	Remote Similarity	NPD2067	Discontinued
0.672	Remote Similarity	NPD3021	Approved
0.672	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3022	Approved
0.6719	Remote Similarity	NPD4766	Approved
0.6713	Remote Similarity	NPD2346	Discontinued
0.6692	Remote Similarity	NPD6065	Approved
0.6691	Remote Similarity	NPD6233	Phase 2
0.669	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4110	Phase 3
0.669	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3643	Approved
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD3644	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD5667	Approved
0.6667	Remote Similarity	NPD3642	Approved
0.6645	Remote Similarity	NPD37	Approved
0.6643	Remote Similarity	NPD3620	Phase 2
0.6643	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4476	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