NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	644.26
Volume:	659.354
LogP:	4.72
LogD:	3.607
LogS:	-5.546
# Rotatable Bonds:	10
TPSA:	118.98
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.206
Synthetic Accessibility Score:	4.514
Fsp3:	0.351
Lipinski Rule-of-5:	Accepted
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:	-4.808
MDCK Permeability:	2.501266499166377e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	90.27945709228516%
Volume Distribution (VD):	0.413
Pgp-substrate:	11.557461738586426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.37
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	5.293
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.819
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.295
Skin Sensitization:	0.066
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.152
Respiratory Toxicity:	0.597

Download Data

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

Natural Product: NPC477883

Natural Product ID:	NPC477883
*Common Name:**	[(8S,9S,10S,11R)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(E)-2-methylbut-2-enoyl]-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] (E)-3-phenylprop-2-enoate
IUPAC Name:	[(8S,9S,10S,11R)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(E)-2-methylbut-2-enoyl]-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] (E)-3-phenylprop-2-enoate
Synonyms:	Tiegusanin G
Standard InCHIKey:	AXPBCKBCCYODQS-ZIRAGJQESA-N
Standard InCHI:	InChI=1S/C37H40O10/c1-9-20(2)31(39)30-23-17-25(41-5)33(42-6)35(43-7)28(23)29-24(18-26-34(36(29)44-8)46-19-45-26)32(21(3)37(30,4)40)47-27(38)16-15-22-13-11-10-12-14-22/h9-18,21,30,32,40H,19H2,1-8H3/b16-15+,20-9+/t21-,30+,32+,37-/m0/s1
SMILES:	C/C=C(\C)/C(=O)[C@H]1C2=CC(=C(C(=C2C3=C(C4=C(C=C3[C@@H]([C@@H]([C@]1(C)O)C)OC(=O)/C=C/C5=CC=CC=C5)OCO4)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45268361
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	>	200000	nM	PMID[19413342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	7900	nM	PMID[19413342]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	25.2	n.a.	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 NPC477883 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	377
0.1-0.2	1459
0.2-0.3	3038
0.3-0.4	7109
0.4-0.5	10641
0.5-0.6	4760
0.6-0.7	5252
0.7-0.8	8520
0.8-0.85	1394
0.85-0.9	113
0.9-0.95	30
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC477881
0.9695	High Similarity	NPC477882
0.9695	High Similarity	NPC477880
0.9503	High Similarity	NPC477884
0.9444	High Similarity	NPC118162
0.9444	High Similarity	NPC320471
0.9444	High Similarity	NPC83049
0.9371	High Similarity	NPC477885
0.9317	High Similarity	NPC319749
0.9308	High Similarity	NPC477380
0.9268	High Similarity	NPC79322
0.9217	High Similarity	NPC469506
0.9212	High Similarity	NPC88557
0.9152	High Similarity	NPC311912
0.9141	High Similarity	NPC469512
0.9141	High Similarity	NPC280778
0.9119	High Similarity	NPC477377
0.9085	High Similarity	NPC469518
0.9085	High Similarity	NPC469475
0.908	High Similarity	NPC258322
0.908	High Similarity	NPC191352
0.9074	High Similarity	NPC325122
0.9057	High Similarity	NPC477378
0.9057	High Similarity	NPC475229
0.9	High Similarity	NPC217708
0.9	High Similarity	NPC77237
0.9	High Similarity	NPC53669
0.9	High Similarity	NPC126405
0.9	High Similarity	NPC297271
0.9	High Similarity	NPC308739
0.9	High Similarity	NPC16791
0.897	High Similarity	NPC291977
0.8957	High Similarity	NPC215400
0.8957	High Similarity	NPC230531
0.8931	High Similarity	NPC316989
0.8922	High Similarity	NPC471180
0.8909	High Similarity	NPC61141
0.8909	High Similarity	NPC42797
0.8909	High Similarity	NPC473445
0.8896	High Similarity	NPC475592
0.8882	High Similarity	NPC474514
0.8882	High Similarity	NPC24562
0.8876	High Similarity	NPC178737
0.8875	High Similarity	NPC224472
0.8868	High Similarity	NPC322426
0.8868	High Similarity	NPC477374
0.8868	High Similarity	NPC477376
0.8855	High Similarity	NPC475865
0.8841	High Similarity	NPC328122
0.8827	High Similarity	NPC178195
0.8827	High Similarity	NPC348849
0.8827	High Similarity	NPC198461
0.8824	High Similarity	NPC474568
0.8805	High Similarity	NPC327352
0.8805	High Similarity	NPC252281
0.8805	High Similarity	NPC198129
0.8805	High Similarity	NPC477375
0.8795	High Similarity	NPC249070
0.8773	High Similarity	NPC238834
0.8773	High Similarity	NPC476065
0.8765	High Similarity	NPC471181
0.872	High Similarity	NPC469474
0.872	High Similarity	NPC301897
0.872	High Similarity	NPC473323
0.8712	High Similarity	NPC473736
0.8712	High Similarity	NPC312763
0.8704	High Similarity	NPC220577
0.8679	High Similarity	NPC321696
0.8679	High Similarity	NPC321958
0.8675	High Similarity	NPC474770
0.865	High Similarity	NPC475141
0.865	High Similarity	NPC474606
0.8642	High Similarity	NPC303519
0.8634	High Similarity	NPC85141
0.8629	High Similarity	NPC35924
0.8629	High Similarity	NPC199172
0.8625	High Similarity	NPC295297
0.8623	High Similarity	NPC239890
0.8623	High Similarity	NPC209411
0.8616	High Similarity	NPC327651
0.8616	High Similarity	NPC318286
0.8614	High Similarity	NPC125713
0.8606	High Similarity	NPC29727
0.8598	High Similarity	NPC473425
0.8598	High Similarity	NPC273578
0.8589	High Similarity	NPC471154
0.8588	High Similarity	NPC42230
0.858	High Similarity	NPC475738
0.858	High Similarity	NPC474647
0.858	High Similarity	NPC475953
0.8571	High Similarity	NPC469371
0.8571	High Similarity	NPC316676
0.8571	High Similarity	NPC325720
0.8571	High Similarity	NPC304821
0.8563	High Similarity	NPC96593
0.8563	High Similarity	NPC267549
0.8554	High Similarity	NPC19947
0.8554	High Similarity	NPC207584
0.8553	High Similarity	NPC326144
0.8553	High Similarity	NPC474036
0.8537	High Similarity	NPC245948
0.8529	High Similarity	NPC474042
0.8529	High Similarity	NPC174734
0.8528	High Similarity	NPC475756
0.8528	High Similarity	NPC62354
0.8521	High Similarity	NPC223006
0.8521	High Similarity	NPC272750
0.8521	High Similarity	NPC173729
0.8521	High Similarity	NPC134047
0.8512	High Similarity	NPC288149
0.8506	High Similarity	NPC67629
0.8506	High Similarity	NPC79736
0.8506	High Similarity	NPC196771
0.8506	High Similarity	NPC472723
0.8497	Intermediate Similarity	NPC88560
0.8497	Intermediate Similarity	NPC172033
0.8497	Intermediate Similarity	NPC175230
0.8494	Intermediate Similarity	NPC237946
0.8494	Intermediate Similarity	NPC32373
0.8491	Intermediate Similarity	NPC76415
0.8491	Intermediate Similarity	NPC218510
0.8488	Intermediate Similarity	NPC180768
0.8488	Intermediate Similarity	NPC212748
0.8483	Intermediate Similarity	NPC65489
0.848	Intermediate Similarity	NPC474948
0.8476	Intermediate Similarity	NPC476434
0.8476	Intermediate Similarity	NPC56184
0.8476	Intermediate Similarity	NPC104353
0.8475	Intermediate Similarity	NPC231254
0.8466	Intermediate Similarity	NPC170203
0.8466	Intermediate Similarity	NPC473989
0.8466	Intermediate Similarity	NPC470916
0.8462	Intermediate Similarity	NPC144557
0.8462	Intermediate Similarity	NPC76687
0.8462	Intermediate Similarity	NPC125991
0.8452	Intermediate Similarity	NPC63061
0.8448	Intermediate Similarity	NPC107739
0.8448	Intermediate Similarity	NPC469354
0.8447	Intermediate Similarity	NPC87295
0.8444	Intermediate Similarity	NPC264302
0.8439	Intermediate Similarity	NPC235575
0.8439	Intermediate Similarity	NPC261254
0.8439	Intermediate Similarity	NPC38438
0.8438	Intermediate Similarity	NPC18211
0.8438	Intermediate Similarity	NPC143092
0.843	Intermediate Similarity	NPC117911
0.843	Intermediate Similarity	NPC473202
0.8424	Intermediate Similarity	NPC68882
0.8424	Intermediate Similarity	NPC35544
0.8424	Intermediate Similarity	NPC308555
0.8424	Intermediate Similarity	NPC104728
0.8421	Intermediate Similarity	NPC113093
0.8418	Intermediate Similarity	NPC473883
0.8415	Intermediate Similarity	NPC234152
0.8415	Intermediate Similarity	NPC477379
0.8415	Intermediate Similarity	NPC475460
0.8415	Intermediate Similarity	NPC13985
0.8415	Intermediate Similarity	NPC210642
0.8409	Intermediate Similarity	NPC472726
0.8409	Intermediate Similarity	NPC472725
0.8409	Intermediate Similarity	NPC471030
0.8405	Intermediate Similarity	NPC474347
0.8405	Intermediate Similarity	NPC474393
0.8405	Intermediate Similarity	NPC477698
0.8402	Intermediate Similarity	NPC34376
0.8402	Intermediate Similarity	NPC94155
0.8402	Intermediate Similarity	NPC92589
0.8402	Intermediate Similarity	NPC100465
0.8402	Intermediate Similarity	NPC152424
0.84	Intermediate Similarity	NPC23593
0.84	Intermediate Similarity	NPC263955
0.84	Intermediate Similarity	NPC473713
0.8395	Intermediate Similarity	NPC183083
0.8395	Intermediate Similarity	NPC153620
0.8395	Intermediate Similarity	NPC137352
0.8395	Intermediate Similarity	NPC24257
0.8393	Intermediate Similarity	NPC474043
0.8393	Intermediate Similarity	NPC62518
0.8393	Intermediate Similarity	NPC215375
0.8393	Intermediate Similarity	NPC173726
0.8393	Intermediate Similarity	NPC241600
0.8391	Intermediate Similarity	NPC316539
0.8391	Intermediate Similarity	NPC472993
0.8389	Intermediate Similarity	NPC201814
0.8383	Intermediate Similarity	NPC155063
0.8383	Intermediate Similarity	NPC109765
0.8383	Intermediate Similarity	NPC227062
0.8382	Intermediate Similarity	NPC476365
0.8382	Intermediate Similarity	NPC149011
0.8382	Intermediate Similarity	NPC204937
0.838	Intermediate Similarity	NPC260521
0.838	Intermediate Similarity	NPC475360
0.838	Intermediate Similarity	NPC469649
0.8373	Intermediate Similarity	NPC57211
0.8373	Intermediate Similarity	NPC478213
0.8372	Intermediate Similarity	NPC116745
0.8372	Intermediate Similarity	NPC150131
0.8364	Intermediate Similarity	NPC151425
0.8364	Intermediate Similarity	NPC267091
0.8363	Intermediate Similarity	NPC7752

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 NPC477883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	906
0.2-0.3	1674
0.3-0.4	2629
0.4-0.5	1960
0.5-0.6	1017
0.6-0.7	454
0.7-0.8	157
0.8-0.85	22
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD7199	Phase 2
0.8571	High Similarity	NPD6980	Clinical (unspecified phase)
0.8537	High Similarity	NPD37	Approved
0.8529	High Similarity	NPD7473	Discontinued
0.8521	High Similarity	NPD7184	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD4966	Approved
0.8494	Intermediate Similarity	NPD4965	Approved
0.8494	Intermediate Similarity	NPD4967	Phase 2
0.8393	Intermediate Similarity	NPD6234	Discontinued
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8353	Intermediate Similarity	NPD6232	Discontinued
0.8305	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7819	Suspended
0.8218	Intermediate Similarity	NPD5844	Phase 1
0.8171	Intermediate Similarity	NPD7074	Phase 3
0.8161	Intermediate Similarity	NPD7228	Approved
0.8114	Intermediate Similarity	NPD7054	Approved
0.8107	Intermediate Similarity	NPD3817	Phase 2
0.8068	Intermediate Similarity	NPD7472	Approved
0.8066	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD1934	Approved
0.7978	Intermediate Similarity	NPD6559	Discontinued
0.7978	Intermediate Similarity	NPD7240	Approved
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7933	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7251	Discontinued
0.7849	Intermediate Similarity	NPD3882	Suspended
0.7836	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6797	Phase 2
0.7803	Intermediate Similarity	NPD3749	Approved
0.7803	Intermediate Similarity	NPD7075	Discontinued
0.7791	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7753	Intermediate Similarity	NPD3751	Discontinued
0.7733	Intermediate Similarity	NPD2801	Approved
0.7733	Intermediate Similarity	NPD1465	Phase 2
0.7727	Intermediate Similarity	NPD7229	Phase 3
0.7727	Intermediate Similarity	NPD3787	Discontinued
0.7722	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7411	Suspended
0.7709	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.767	Intermediate Similarity	NPD6959	Discontinued
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7661	Intermediate Similarity	NPD4380	Phase 2
0.7657	Intermediate Similarity	NPD919	Approved
0.7644	Intermediate Similarity	NPD7768	Phase 2
0.7641	Intermediate Similarity	NPD8151	Discontinued
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD8455	Phase 2
0.7619	Intermediate Similarity	NPD6799	Approved
0.7574	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD2532	Approved
0.7572	Intermediate Similarity	NPD6801	Discontinued
0.7571	Intermediate Similarity	NPD8127	Discontinued
0.7558	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1511	Approved
0.7515	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7474	Intermediate Similarity	NPD7680	Approved
0.7471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1510	Phase 2
0.7442	Intermediate Similarity	NPD1653	Approved
0.744	Intermediate Similarity	NPD3750	Approved
0.7427	Intermediate Similarity	NPD1512	Approved
0.7425	Intermediate Similarity	NPD1549	Phase 2
0.7396	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD5402	Approved
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1247	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3748	Approved
0.7347	Intermediate Similarity	NPD7871	Phase 2
0.7347	Intermediate Similarity	NPD7870	Phase 2
0.7317	Intermediate Similarity	NPD1240	Approved
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7299	Intermediate Similarity	NPD3226	Approved
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD5403	Approved
0.7283	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD5401	Approved
0.7262	Intermediate Similarity	NPD7266	Discontinued
0.7257	Intermediate Similarity	NPD7028	Phase 2
0.725	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5006	Approved
0.7245	Intermediate Similarity	NPD5005	Approved
0.7235	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6782	Approved
0.7231	Intermediate Similarity	NPD6781	Approved
0.7231	Intermediate Similarity	NPD6780	Approved
0.7231	Intermediate Similarity	NPD6777	Approved
0.7231	Intermediate Similarity	NPD6776	Approved
0.7231	Intermediate Similarity	NPD6778	Approved
0.7231	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD1607	Approved
0.7202	Intermediate Similarity	NPD6099	Approved
0.7202	Intermediate Similarity	NPD6100	Approved
0.7202	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5242	Approved
0.7195	Intermediate Similarity	NPD3764	Approved
0.7192	Intermediate Similarity	NPD7930	Approved
0.7191	Intermediate Similarity	NPD5353	Approved
0.7176	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7172	Intermediate Similarity	NPD8320	Phase 1
0.7172	Intermediate Similarity	NPD8319	Approved
0.717	Intermediate Similarity	NPD3705	Approved
0.7169	Intermediate Similarity	NPD230	Phase 1
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7168	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD3027	Phase 3
0.7129	Intermediate Similarity	NPD7801	Approved
0.7128	Intermediate Similarity	NPD4420	Approved
0.711	Intermediate Similarity	NPD7390	Discontinued
0.7101	Intermediate Similarity	NPD2438	Suspended
0.7091	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD7799	Discontinued
0.7074	Intermediate Similarity	NPD7549	Discontinued
0.7071	Intermediate Similarity	NPD6823	Phase 2
0.7066	Intermediate Similarity	NPD447	Suspended
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2798	Approved
0.7049	Intermediate Similarity	NPD5711	Approved
0.7049	Intermediate Similarity	NPD5710	Approved
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7041	Intermediate Similarity	NPD7700	Phase 2
0.7041	Intermediate Similarity	NPD7699	Phase 2
0.7035	Intermediate Similarity	NPD7003	Approved
0.7035	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4110	Phase 3
0.7035	Intermediate Similarity	NPD8166	Discontinued
0.7029	Intermediate Similarity	NPD6273	Approved
0.7022	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD6385	Approved
0.7019	Intermediate Similarity	NPD1608	Approved
0.7017	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD943	Approved
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD8407	Phase 2
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3268	Approved
0.6986	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7097	Phase 1
0.6974	Remote Similarity	NPD6535	Approved
0.6974	Remote Similarity	NPD6534	Approved
0.697	Remote Similarity	NPD4908	Phase 1
0.697	Remote Similarity	NPD6832	Phase 2
0.6965	Remote Similarity	NPD7999	Approved
0.6959	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7296	Approved
0.6959	Remote Similarity	NPD2344	Approved
0.6946	Remote Similarity	NPD6233	Phase 2
0.6943	Remote Similarity	NPD4287	Approved
0.6941	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1283	Approved
0.6931	Remote Similarity	NPD8368	Discontinued
0.6927	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6971	Discontinued
0.6905	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2979	Phase 3
0.6901	Remote Similarity	NPD5404	Approved
0.6901	Remote Similarity	NPD5405	Approved
0.6901	Remote Similarity	NPD5406	Approved
0.6901	Remote Similarity	NPD5408	Approved
0.6898	Remote Similarity	NPD7893	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