NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	634.28
Volume:	647.331
LogP:	5.577
LogD:	4.041
LogS:	-5.545
# Rotatable Bonds:	12
TPSA:	118.98
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.275
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	2.8776486942660995e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	88.73477172851562%
Volume Distribution (VD):	0.508
Pgp-substrate:	4.147172451019287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.964
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	4.435
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.12
Skin Sensitization:	0.032
Carcinogencity:	0.037
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.354

Download Data

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

Natural Product: NPC477881

Natural Product ID:	NPC477881
*Common Name:**	[(8S,9S,10S,11R)-8-benzoyl-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] hexanoate
IUPAC Name:	[(8S,9S,10S,11R)-8-benzoyl-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] hexanoate
Synonyms:	Tiegusanin E
Standard InCHIKey:	UHZVOOFMWZABRC-BHNQFKMUSA-N
Standard InCHI:	InChI=1S/C36H42O10/c1-8-9-11-16-26(37)46-31-20(2)36(3,39)29(30(38)21-14-12-10-13-15-21)22-17-24(40-4)32(41-5)34(42-6)27(22)28-23(31)18-25-33(35(28)43-7)45-19-44-25/h10,12-15,17-18,20,29,31,39H,8-9,11,16,19H2,1-7H3/t20-,29+,31+,36-/m0/s1
SMILES:	CCCCCC(=O)O[C@@H]1[C@@H]([C@]([C@H](C2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)OC)OC)OC)OC)C(=O)C5=CC=CC=C5)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45270921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7850	Schisandra propinqua	Species	Schisandraceae	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
EC50	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
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	118700	nM	PMID[19413342]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	4.1	n.a.	PMID[19413342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	28700	nM	PMID[19413342]

☑ 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 NPC477881 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	379
0.1-0.2	1498
0.2-0.3	3104
0.3-0.4	7375
0.4-0.5	10551
0.5-0.6	4491
0.6-0.7	5071
0.7-0.8	8061
0.8-0.85	1962
0.85-0.9	176
0.9-0.95	21
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC477883
0.9817	High Similarity	NPC477882
0.9817	High Similarity	NPC477880
0.9627	High Similarity	NPC477884
0.9568	High Similarity	NPC83049
0.9568	High Similarity	NPC118162
0.9568	High Similarity	NPC320471
0.9441	High Similarity	NPC319749
0.939	High Similarity	NPC79322
0.9337	High Similarity	NPC469506
0.9333	High Similarity	NPC88557
0.9273	High Similarity	NPC311912
0.9264	High Similarity	NPC280778
0.9255	High Similarity	NPC477885
0.9202	High Similarity	NPC258322
0.9202	High Similarity	NPC191352
0.9198	High Similarity	NPC325122
0.9193	High Similarity	NPC477380
0.9091	High Similarity	NPC291977
0.9042	High Similarity	NPC471180
0.903	High Similarity	NPC469512
0.903	High Similarity	NPC61141
0.903	High Similarity	NPC473445
0.903	High Similarity	NPC42797
0.9006	High Similarity	NPC477377
0.8994	High Similarity	NPC178737
0.8976	High Similarity	NPC475865
0.8976	High Similarity	NPC469518
0.8976	High Similarity	NPC469475
0.8963	High Similarity	NPC328122
0.8944	High Similarity	NPC477378
0.8944	High Similarity	NPC475229
0.8916	High Similarity	NPC249070
0.8889	High Similarity	NPC308739
0.8889	High Similarity	NPC77237
0.8889	High Similarity	NPC297271
0.8889	High Similarity	NPC217708
0.8889	High Similarity	NPC16791
0.8889	High Similarity	NPC53669
0.8889	High Similarity	NPC126405
0.8882	High Similarity	NPC471181
0.8848	High Similarity	NPC215400
0.8848	High Similarity	NPC230531
0.8841	High Similarity	NPC301897
0.8827	High Similarity	NPC220577
0.882	High Similarity	NPC316989
0.8795	High Similarity	NPC474770
0.8788	High Similarity	NPC475592
0.8773	High Similarity	NPC24562
0.8773	High Similarity	NPC474514
0.8765	High Similarity	NPC224472
0.8758	High Similarity	NPC477376
0.8758	High Similarity	NPC322426
0.8758	High Similarity	NPC477374
0.8743	High Similarity	NPC209411
0.8743	High Similarity	NPC35924
0.8743	High Similarity	NPC199172
0.8743	High Similarity	NPC239890
0.8735	High Similarity	NPC125713
0.8721	High Similarity	NPC474568
0.872	High Similarity	NPC348849
0.872	High Similarity	NPC178195
0.872	High Similarity	NPC198461
0.8698	High Similarity	NPC475738
0.8696	High Similarity	NPC477375
0.8696	High Similarity	NPC252281
0.8696	High Similarity	NPC327352
0.8696	High Similarity	NPC198129
0.8686	High Similarity	NPC469371
0.8678	High Similarity	NPC267549
0.8667	High Similarity	NPC238834
0.8667	High Similarity	NPC476065
0.865	High Similarity	NPC62354
0.8647	High Similarity	NPC174734
0.8647	High Similarity	NPC474042
0.8621	High Similarity	NPC196771
0.8621	High Similarity	NPC472723
0.8621	High Similarity	NPC67629
0.8621	High Similarity	NPC79736
0.8614	High Similarity	NPC469474
0.8614	High Similarity	NPC473323
0.8613	High Similarity	NPC88560
0.8613	High Similarity	NPC172033
0.8613	High Similarity	NPC175230
0.8606	High Similarity	NPC473736
0.8606	High Similarity	NPC312763
0.8605	High Similarity	NPC212748
0.8605	High Similarity	NPC180768
0.8598	High Similarity	NPC104353
0.8596	High Similarity	NPC65489
0.8588	High Similarity	NPC231254
0.858	High Similarity	NPC125991
0.858	High Similarity	NPC76687
0.858	High Similarity	NPC170203
0.8571	High Similarity	NPC321696
0.8571	High Similarity	NPC321958
0.8563	High Similarity	NPC469354
0.8556	High Similarity	NPC264302
0.8555	High Similarity	NPC261254
0.8555	High Similarity	NPC235575
0.8555	High Similarity	NPC38438
0.8547	High Similarity	NPC117911
0.8547	High Similarity	NPC473202
0.8545	High Similarity	NPC308555
0.8545	High Similarity	NPC474606
0.8545	High Similarity	NPC68882
0.8545	High Similarity	NPC104728
0.8545	High Similarity	NPC475141
0.8545	High Similarity	NPC35544
0.8538	High Similarity	NPC113093
0.8537	High Similarity	NPC475460
0.8537	High Similarity	NPC234152
0.8537	High Similarity	NPC303519
0.8531	High Similarity	NPC473883
0.8528	High Similarity	NPC85141
0.8523	High Similarity	NPC471030
0.8523	High Similarity	NPC472726
0.8523	High Similarity	NPC472725
0.8521	High Similarity	NPC34376
0.8521	High Similarity	NPC92589
0.8521	High Similarity	NPC94155
0.8519	High Similarity	NPC295297
0.8519	High Similarity	NPC24257
0.8519	High Similarity	NPC153620
0.8514	High Similarity	NPC473713
0.8512	High Similarity	NPC62518
0.8512	High Similarity	NPC215375
0.8512	High Similarity	NPC474043
0.8509	High Similarity	NPC327651
0.8509	High Similarity	NPC318286
0.8506	High Similarity	NPC472993
0.8506	High Similarity	NPC316539
0.8503	High Similarity	NPC155063
0.8503	High Similarity	NPC109765
0.8503	High Similarity	NPC29727
0.8503	High Similarity	NPC227062
0.85	High Similarity	NPC201814
0.8497	Intermediate Similarity	NPC204937
0.8497	Intermediate Similarity	NPC149011
0.8497	Intermediate Similarity	NPC476365
0.8494	Intermediate Similarity	NPC273578
0.8494	Intermediate Similarity	NPC57211
0.8494	Intermediate Similarity	NPC478213
0.8494	Intermediate Similarity	NPC473425
0.8492	Intermediate Similarity	NPC475360
0.8492	Intermediate Similarity	NPC260521
0.8492	Intermediate Similarity	NPC469649
0.8488	Intermediate Similarity	NPC42230
0.8488	Intermediate Similarity	NPC116745
0.8488	Intermediate Similarity	NPC150131
0.8485	Intermediate Similarity	NPC151425
0.8485	Intermediate Similarity	NPC267091
0.8485	Intermediate Similarity	NPC471154
0.848	Intermediate Similarity	NPC474647
0.848	Intermediate Similarity	NPC474301
0.848	Intermediate Similarity	NPC7752
0.848	Intermediate Similarity	NPC475953
0.8475	Intermediate Similarity	NPC53680
0.8475	Intermediate Similarity	NPC208797
0.8471	Intermediate Similarity	NPC478199
0.8471	Intermediate Similarity	NPC472964
0.8471	Intermediate Similarity	NPC414831
0.8471	Intermediate Similarity	NPC116838
0.8471	Intermediate Similarity	NPC22130
0.8471	Intermediate Similarity	NPC469575
0.8466	Intermediate Similarity	NPC472387
0.8466	Intermediate Similarity	NPC477895
0.8466	Intermediate Similarity	NPC325720
0.8466	Intermediate Similarity	NPC469418
0.8466	Intermediate Similarity	NPC316676
0.8466	Intermediate Similarity	NPC304821
0.8466	Intermediate Similarity	NPC241196
0.8462	Intermediate Similarity	NPC239818
0.8462	Intermediate Similarity	NPC78944
0.8462	Intermediate Similarity	NPC472055
0.8462	Intermediate Similarity	NPC218471
0.8462	Intermediate Similarity	NPC96593
0.8462	Intermediate Similarity	NPC299436
0.8457	Intermediate Similarity	NPC146803
0.8457	Intermediate Similarity	NPC296575
0.8457	Intermediate Similarity	NPC213482
0.8452	Intermediate Similarity	NPC207584
0.8452	Intermediate Similarity	NPC108456
0.8452	Intermediate Similarity	NPC222689
0.8452	Intermediate Similarity	NPC258644
0.8452	Intermediate Similarity	NPC35598
0.8452	Intermediate Similarity	NPC167595
0.8452	Intermediate Similarity	NPC474990
0.8452	Intermediate Similarity	NPC202495
0.8452	Intermediate Similarity	NPC19947
0.8448	Intermediate Similarity	NPC223375
0.8448	Intermediate Similarity	NPC67134
0.8448	Intermediate Similarity	NPC475825
0.8448	Intermediate Similarity	NPC47140
0.8447	Intermediate Similarity	NPC326144
0.8447	Intermediate Similarity	NPC474036
0.8444	Intermediate Similarity	NPC240200
0.8444	Intermediate Similarity	NPC290289
0.8444	Intermediate Similarity	NPC223534
0.8444	Intermediate Similarity	NPC158214

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 NPC477881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	917
0.2-0.3	1673
0.3-0.4	2612
0.4-0.5	1984
0.5-0.6	996
0.6-0.7	443
0.7-0.8	161
0.8-0.85	29
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD6980	Clinical (unspecified phase)
0.8647	High Similarity	NPD7473	Discontinued
0.8521	High Similarity	NPD7199	Phase 2
0.8488	Intermediate Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD6232	Discontinued
0.8434	Intermediate Similarity	NPD37	Approved
0.8421	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD4965	Approved
0.8393	Intermediate Similarity	NPD4967	Phase 2
0.8393	Intermediate Similarity	NPD4966	Approved
0.8383	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8294	Intermediate Similarity	NPD6234	Discontinued
0.8286	Intermediate Similarity	NPD7074	Phase 3
0.8229	Intermediate Similarity	NPD7054	Approved
0.8225	Intermediate Similarity	NPD3817	Phase 2
0.8212	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7472	Approved
0.8177	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7808	Phase 3
0.814	Intermediate Similarity	NPD5494	Approved
0.8107	Intermediate Similarity	NPD1934	Approved
0.809	Intermediate Similarity	NPD6559	Discontinued
0.8068	Intermediate Similarity	NPD7228	Approved
0.8057	Intermediate Similarity	NPD6166	Phase 2
0.8057	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD3882	Suspended
0.7953	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6797	Phase 2
0.7919	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD7075	Discontinued
0.7907	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7685	Pre-registration
0.7889	Intermediate Similarity	NPD7240	Approved
0.7849	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD2801	Approved
0.7836	Intermediate Similarity	NPD7411	Suspended
0.7833	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD8313	Approved
0.7802	Intermediate Similarity	NPD8312	Approved
0.7797	Intermediate Similarity	NPD3926	Phase 2
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7772	Intermediate Similarity	NPD8434	Phase 2
0.7771	Intermediate Similarity	NPD919	Approved
0.7759	Intermediate Similarity	NPD7768	Phase 2
0.7758	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8151	Discontinued
0.7738	Intermediate Similarity	NPD6799	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7674	Intermediate Similarity	NPD6599	Discontinued
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD3787	Discontinued
0.764	Intermediate Similarity	NPD7229	Phase 3
0.7636	Intermediate Similarity	NPD2796	Approved
0.7633	Intermediate Similarity	NPD1511	Approved
0.7616	Intermediate Similarity	NPD7458	Discontinued
0.7588	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.756	Intermediate Similarity	NPD3750	Approved
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7544	Intermediate Similarity	NPD1512	Approved
0.7543	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD1247	Approved
0.7486	Intermediate Similarity	NPD8127	Discontinued
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3748	Approved
0.7449	Intermediate Similarity	NPD7870	Phase 2
0.7449	Intermediate Similarity	NPD7871	Phase 2
0.7439	Intermediate Similarity	NPD1240	Approved
0.7423	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3226	Approved
0.74	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7783	Phase 2
0.7399	Intermediate Similarity	NPD5403	Approved
0.7399	Intermediate Similarity	NPD920	Approved
0.7398	Intermediate Similarity	NPD7680	Approved
0.7398	Intermediate Similarity	NPD7696	Phase 3
0.7398	Intermediate Similarity	NPD7698	Approved
0.7398	Intermediate Similarity	NPD7697	Approved
0.7394	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD1933	Approved
0.7384	Intermediate Similarity	NPD5401	Approved
0.7384	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1653	Approved
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7353	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7874	Approved
0.7349	Intermediate Similarity	NPD1607	Approved
0.7347	Intermediate Similarity	NPD5006	Approved
0.7347	Intermediate Similarity	NPD5005	Approved
0.7333	Intermediate Similarity	NPD6782	Approved
0.7333	Intermediate Similarity	NPD6781	Approved
0.7333	Intermediate Similarity	NPD6778	Approved
0.7333	Intermediate Similarity	NPD6777	Approved
0.7333	Intermediate Similarity	NPD6780	Approved
0.7333	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD6779	Approved
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7317	Intermediate Similarity	NPD3764	Approved
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6190	Approved
0.7308	Intermediate Similarity	NPD5242	Approved
0.7303	Intermediate Similarity	NPD5353	Approved
0.7294	Intermediate Similarity	NPD1243	Approved
0.7291	Intermediate Similarity	NPD7930	Approved
0.7289	Intermediate Similarity	NPD230	Phase 1
0.7283	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8320	Phase 1
0.7273	Intermediate Similarity	NPD8319	Approved
0.7267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7701	Phase 2
0.7231	Intermediate Similarity	NPD4420	Approved
0.7228	Intermediate Similarity	NPD7801	Approved
0.7225	Intermediate Similarity	NPD7390	Discontinued
0.7189	Intermediate Similarity	NPD7799	Discontinued
0.7186	Intermediate Similarity	NPD447	Suspended
0.7178	Intermediate Similarity	NPD2798	Approved
0.7176	Intermediate Similarity	NPD7266	Discontinued
0.7176	Intermediate Similarity	NPD2346	Discontinued
0.7175	Intermediate Similarity	NPD7028	Phase 2
0.7172	Intermediate Similarity	NPD6823	Phase 2
0.716	Intermediate Similarity	NPD2799	Discontinued
0.7158	Intermediate Similarity	NPD5710	Approved
0.7158	Intermediate Similarity	NPD5711	Approved
0.7157	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7126	Intermediate Similarity	NPD943	Approved
0.7118	Intermediate Similarity	NPD1551	Phase 2
0.7118	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD6099	Approved
0.7105	Intermediate Similarity	NPD8407	Phase 2
0.7093	Intermediate Similarity	NPD6674	Discontinued
0.7092	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD3705	Approved
0.7081	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6534	Approved
0.7077	Intermediate Similarity	NPD6535	Approved
0.7076	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2344	Approved
0.7065	Intermediate Similarity	NPD7999	Approved
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3027	Phase 3
0.7047	Intermediate Similarity	NPD4287	Approved
0.7037	Intermediate Similarity	NPD8368	Discontinued
0.7018	Intermediate Similarity	NPD2438	Suspended
0.7018	Intermediate Similarity	NPD5405	Approved
0.7018	Intermediate Similarity	NPD5404	Approved
0.7018	Intermediate Similarity	NPD5406	Approved
0.7018	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7005	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7549	Discontinued
0.6994	Remote Similarity	NPD2800	Approved
0.6989	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5953	Discontinued
0.6971	Remote Similarity	NPD8404	Phase 2
0.6968	Remote Similarity	NPD7286	Phase 2
0.6961	Remote Similarity	NPD5761	Phase 2
0.6961	Remote Similarity	NPD5760	Phase 2
0.6959	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4110	Phase 3
0.6954	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8166	Discontinued
0.6946	Remote Similarity	NPD7584	Approved
0.6941	Remote Similarity	NPD6651	Approved
0.694	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD1613	Approved
0.6923	Remote Similarity	NPD1612	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