NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	602.25
Volume:	618.608
LogP:	5.088
LogD:	4.744
LogS:	-5.723
# Rotatable Bonds:	9
TPSA:	98.75
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.201
Synthetic Accessibility Score:	4.329
Fsp3:	0.371
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:	-4.851
MDCK Permeability:	2.3999162294785492e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	90.95217895507812%
Volume Distribution (VD):	0.338
Pgp-substrate:	7.326213836669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.976
CYP2C19-substrate:	0.915
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.776
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.341
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	5.422
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.784
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.036
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.161

Download Data

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

Natural Product: NPC477884

Natural Product ID:	NPC477884
*Common Name:**	[(8R,9R,10R,11R)-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] benzoate
IUPAC Name:	[(8R,9R,10R,11R)-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] benzoate
Synonyms:	Tiegusanin H
Standard InCHIKey:	PAXYJONJODVBCT-ZLJVZANUSA-N
Standard InCHI:	InChI=1S/C35H38O9/c1-9-18(2)29(36)26-19(3)20(4)30(44-35(37)21-13-11-10-12-14-21)23-16-25-32(43-17-42-25)34(41-8)28(23)27-22(26)15-24(38-5)31(39-6)33(27)40-7/h9-16,19-20,26,30H,17H2,1-8H3/b18-9+/t19-,20-,26-,30-/m1/s1
SMILES:	C/C=C(\C)/C(=O)[C@@H]1[C@@H]([C@H]([C@H](C2=CC3=C(C(=C2C4=C(C(=C(C=C14)OC)OC)OC)OC)OCO3)OC(=O)C5=CC=CC=C5)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45268362
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	=	78200	nM	PMID[19413342]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	5.1	n.a.	PMID[19413342]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15400	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 NPC477884 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	446
0.1-0.2	1545
0.2-0.3	3380
0.3-0.4	8318
0.4-0.5	10250
0.5-0.6	3697
0.6-0.7	5787
0.7-0.8	8247
0.8-0.85	887
0.85-0.9	106
0.9-0.95	26
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC319749
0.9627	High Similarity	NPC477881
0.9613	High Similarity	NPC477885
0.9554	High Similarity	NPC191352
0.9554	High Similarity	NPC258322
0.9551	High Similarity	NPC325122
0.9548	High Similarity	NPC477380
0.9503	High Similarity	NPC477883
0.9494	High Similarity	NPC280778
0.9451	High Similarity	NPC477880
0.9451	High Similarity	NPC477882
0.9437	High Similarity	NPC83049
0.9437	High Similarity	NPC118162
0.9437	High Similarity	NPC320471
0.9355	High Similarity	NPC477377
0.929	High Similarity	NPC475229
0.929	High Similarity	NPC477378
0.9259	High Similarity	NPC311912
0.9259	High Similarity	NPC79322
0.9202	High Similarity	NPC88557
0.9167	High Similarity	NPC220577
0.9161	High Similarity	NPC316989
0.913	High Similarity	NPC61141
0.9097	High Similarity	NPC477374
0.9097	High Similarity	NPC322426
0.9097	High Similarity	NPC477376
0.9091	High Similarity	NPC469506
0.9062	High Similarity	NPC125713
0.9051	High Similarity	NPC178195
0.9051	High Similarity	NPC348849
0.9032	High Similarity	NPC477375
0.9032	High Similarity	NPC327352
0.9032	High Similarity	NPC252281
0.9032	High Similarity	NPC198129
0.9012	High Similarity	NPC473445
0.8957	High Similarity	NPC475865
0.8957	High Similarity	NPC291977
0.8938	High Similarity	NPC301897
0.8924	High Similarity	NPC104353
0.8903	High Similarity	NPC321958
0.8903	High Similarity	NPC321696
0.8896	High Similarity	NPC249070
0.8896	High Similarity	NPC42797
0.8868	High Similarity	NPC474514
0.8861	High Similarity	NPC303519
0.8854	High Similarity	NPC85141
0.8839	High Similarity	NPC327651
0.8839	High Similarity	NPC318286
0.8834	High Similarity	NPC209411
0.8834	High Similarity	NPC239890
0.8827	High Similarity	NPC328122
0.8827	High Similarity	NPC230531
0.8827	High Similarity	NPC215400
0.8827	High Similarity	NPC474043
0.8812	High Similarity	NPC273578
0.881	High Similarity	NPC474568
0.8795	High Similarity	NPC471180
0.8774	High Similarity	NPC326144
0.8773	High Similarity	NPC474770
0.875	High Similarity	NPC16791
0.875	High Similarity	NPC217708
0.875	High Similarity	NPC53669
0.875	High Similarity	NPC308739
0.875	High Similarity	NPC178737
0.875	High Similarity	NPC297271
0.875	High Similarity	NPC77237
0.875	High Similarity	NPC24562
0.875	High Similarity	NPC126405
0.8727	High Similarity	NPC469475
0.8727	High Similarity	NPC469518
0.871	High Similarity	NPC76415
0.871	High Similarity	NPC218510
0.8704	High Similarity	NPC115123
0.8704	High Similarity	NPC239113
0.8688	High Similarity	NPC118332
0.8683	High Similarity	NPC475453
0.8683	High Similarity	NPC473531
0.8667	High Similarity	NPC469512
0.8662	High Similarity	NPC87295
0.8655	High Similarity	NPC267549
0.8654	High Similarity	NPC143092
0.8654	High Similarity	NPC18211
0.865	High Similarity	NPC475592
0.8642	High Similarity	NPC238834
0.8642	High Similarity	NPC476065
0.8642	High Similarity	NPC222185
0.8642	High Similarity	NPC234730
0.8639	High Similarity	NPC471181
0.8634	High Similarity	NPC308555
0.8634	High Similarity	NPC68882
0.8625	High Similarity	NPC224472
0.8625	High Similarity	NPC13985
0.8625	High Similarity	NPC210642
0.8623	High Similarity	NPC174734
0.8623	High Similarity	NPC471923
0.8623	High Similarity	NPC474042
0.8608	High Similarity	NPC24257
0.8608	High Similarity	NPC153620
0.8605	High Similarity	NPC472726
0.8605	High Similarity	NPC472725
0.8596	High Similarity	NPC472723
0.8596	High Similarity	NPC196771
0.8596	High Similarity	NPC67629
0.8596	High Similarity	NPC79736
0.8589	High Similarity	NPC473323
0.8589	High Similarity	NPC155063
0.858	High Similarity	NPC478213
0.858	High Similarity	NPC180768
0.858	High Similarity	NPC198461
0.858	High Similarity	NPC312763
0.858	High Similarity	NPC57211
0.8571	High Similarity	NPC42230
0.8563	High Similarity	NPC474647
0.8563	High Similarity	NPC475953
0.8562	High Similarity	NPC149505
0.8554	High Similarity	NPC414831
0.8554	High Similarity	NPC478199
0.8545	High Similarity	NPC78944
0.8544	High Similarity	NPC213482
0.8544	High Similarity	NPC296575
0.8537	High Similarity	NPC82733
0.8537	High Similarity	NPC19600
0.8537	High Similarity	NPC76458
0.8537	High Similarity	NPC258644
0.8535	High Similarity	NPC474036
0.8529	High Similarity	NPC38438
0.8529	High Similarity	NPC473697
0.8528	High Similarity	NPC254163
0.8521	High Similarity	NPC117911
0.8519	High Similarity	NPC475141
0.8519	High Similarity	NPC52623
0.8519	High Similarity	NPC153008
0.8519	High Similarity	NPC148497
0.8519	High Similarity	NPC474606
0.8494	Intermediate Similarity	NPC34376
0.8488	Intermediate Similarity	NPC473713
0.848	Intermediate Similarity	NPC316539
0.8476	Intermediate Similarity	NPC261484
0.8476	Intermediate Similarity	NPC109765
0.8476	Intermediate Similarity	NPC473900
0.8476	Intermediate Similarity	NPC474983
0.8466	Intermediate Similarity	NPC473425
0.8466	Intermediate Similarity	NPC473736
0.8462	Intermediate Similarity	NPC474948
0.8457	Intermediate Similarity	NPC279061
0.8457	Intermediate Similarity	NPC471154
0.8457	Intermediate Similarity	NPC267091
0.8452	Intermediate Similarity	NPC475738
0.8448	Intermediate Similarity	NPC208797
0.8448	Intermediate Similarity	NPC53680
0.8443	Intermediate Similarity	NPC116838
0.8443	Intermediate Similarity	NPC22130
0.8443	Intermediate Similarity	NPC475144
0.8438	Intermediate Similarity	NPC40654
0.8438	Intermediate Similarity	NPC304821
0.8438	Intermediate Similarity	NPC316676
0.8438	Intermediate Similarity	NPC325720
0.8438	Intermediate Similarity	NPC262804
0.8434	Intermediate Similarity	NPC96593
0.843	Intermediate Similarity	NPC469354
0.8428	Intermediate Similarity	NPC224687
0.8424	Intermediate Similarity	NPC474990
0.8424	Intermediate Similarity	NPC19947
0.8424	Intermediate Similarity	NPC202495
0.8424	Intermediate Similarity	NPC207584
0.8418	Intermediate Similarity	NPC475000
0.8415	Intermediate Similarity	NPC478238
0.8415	Intermediate Similarity	NPC284353
0.8412	Intermediate Similarity	NPC477165
0.8405	Intermediate Similarity	NPC475116
0.8405	Intermediate Similarity	NPC245948
0.8402	Intermediate Similarity	NPC475214
0.84	Intermediate Similarity	NPC35924
0.84	Intermediate Similarity	NPC199172
0.8395	Intermediate Similarity	NPC243891
0.8395	Intermediate Similarity	NPC62354
0.8395	Intermediate Similarity	NPC475756
0.8393	Intermediate Similarity	NPC100425
0.8391	Intermediate Similarity	NPC80956
0.8387	Intermediate Similarity	NPC865
0.8383	Intermediate Similarity	NPC15212
0.8383	Intermediate Similarity	NPC288149
0.8383	Intermediate Similarity	NPC296540
0.8383	Intermediate Similarity	NPC309335
0.8382	Intermediate Similarity	NPC297574
0.8375	Intermediate Similarity	NPC104024
0.8375	Intermediate Similarity	NPC80230
0.8375	Intermediate Similarity	NPC65574
0.8375	Intermediate Similarity	NPC101755
0.8375	Intermediate Similarity	NPC304687
0.8375	Intermediate Similarity	NPC295297
0.8373	Intermediate Similarity	NPC113055
0.8372	Intermediate Similarity	NPC175230
0.8372	Intermediate Similarity	NPC172033
0.8372	Intermediate Similarity	NPC88560
0.8365	Intermediate Similarity	NPC474158
0.8365	Intermediate Similarity	NPC184702
0.8365	Intermediate Similarity	NPC27106
0.8365	Intermediate Similarity	NPC470932
0.8364	Intermediate Similarity	NPC32373

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 NPC477884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	935
0.2-0.3	1691
0.3-0.4	2654
0.4-0.5	1937
0.5-0.6	958
0.6-0.7	440
0.7-0.8	151
0.8-0.85	14
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD6980	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7199	Phase 2
0.8405	Intermediate Similarity	NPD37	Approved
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8393	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4966	Approved
0.8364	Intermediate Similarity	NPD4967	Phase 2
0.8364	Intermediate Similarity	NPD4965	Approved
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8263	Intermediate Similarity	NPD6234	Discontinued
0.8246	Intermediate Similarity	NPD3818	Discontinued
0.8225	Intermediate Similarity	NPD6232	Discontinued
0.8214	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7819	Suspended
0.8084	Intermediate Similarity	NPD3817	Phase 2
0.8079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7074	Phase 3
0.8035	Intermediate Similarity	NPD7228	Approved
0.7989	Intermediate Similarity	NPD7054	Approved
0.7944	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7472	Approved
0.791	Intermediate Similarity	NPD7808	Phase 3
0.7861	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD1934	Approved
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.7853	Intermediate Similarity	NPD7240	Approved
0.7836	Intermediate Similarity	NPD919	Approved
0.7816	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6166	Phase 2
0.7811	Intermediate Similarity	NPD1465	Phase 2
0.7809	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7685	Pre-registration
0.7753	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD3748	Approved
0.7719	Intermediate Similarity	NPD3882	Suspended
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2796	Approved
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7663	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2801	Approved
0.76	Intermediate Similarity	NPD7229	Phase 3
0.759	Intermediate Similarity	NPD6799	Approved
0.7588	Intermediate Similarity	NPD7411	Suspended
0.7584	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7458	Discontinued
0.7572	Intermediate Similarity	NPD3749	Approved
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.7558	Intermediate Similarity	NPD5353	Approved
0.7557	Intermediate Similarity	NPD5242	Approved
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.7543	Intermediate Similarity	NPD1247	Approved
0.7543	Intermediate Similarity	NPD6959	Discontinued
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD4380	Phase 2
0.7526	Intermediate Similarity	NPD8151	Discontinued
0.7515	Intermediate Similarity	NPD3750	Approved
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7456	Intermediate Similarity	NPD920	Approved
0.7455	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1933	Approved
0.7446	Intermediate Similarity	NPD8434	Phase 2
0.7443	Intermediate Similarity	NPD8127	Discontinued
0.744	Intermediate Similarity	NPD2534	Approved
0.744	Intermediate Similarity	NPD2532	Approved
0.744	Intermediate Similarity	NPD2533	Approved
0.7396	Intermediate Similarity	NPD5006	Approved
0.7396	Intermediate Similarity	NPD5005	Approved
0.7384	Intermediate Similarity	NPD6385	Approved
0.7384	Intermediate Similarity	NPD6386	Approved
0.7381	Intermediate Similarity	NPD1511	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7680	Approved
0.7356	Intermediate Similarity	NPD5402	Approved
0.7355	Intermediate Similarity	NPD3705	Approved
0.7349	Intermediate Similarity	NPD1243	Approved
0.7337	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD1653	Approved
0.7305	Intermediate Similarity	NPD4628	Phase 3
0.7303	Intermediate Similarity	NPD3787	Discontinued
0.7294	Intermediate Similarity	NPD1512	Approved
0.7289	Intermediate Similarity	NPD1549	Phase 2
0.7277	Intermediate Similarity	NPD4420	Approved
0.7273	Intermediate Similarity	NPD2438	Suspended
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5403	Approved
0.724	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD230	Phase 1
0.7235	Intermediate Similarity	NPD5401	Approved
0.7235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7178	Intermediate Similarity	NPD1240	Approved
0.7168	Intermediate Similarity	NPD3226	Approved
0.716	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7126	Intermediate Similarity	NPD7266	Discontinued
0.7101	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7093	Intermediate Similarity	NPD6273	Approved
0.7092	Intermediate Similarity	NPD7698	Approved
0.7092	Intermediate Similarity	NPD7697	Approved
0.7092	Intermediate Similarity	NPD7696	Phase 3
0.7091	Intermediate Similarity	NPD1607	Approved
0.7074	Intermediate Similarity	NPD8150	Discontinued
0.7073	Intermediate Similarity	NPD2979	Phase 3
0.7066	Intermediate Similarity	NPD2935	Discontinued
0.705	Intermediate Similarity	NPD7874	Approved
0.705	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6674	Discontinued
0.703	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD7028	Phase 2
0.7026	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD6780	Approved
0.7026	Intermediate Similarity	NPD6781	Approved
0.7026	Intermediate Similarity	NPD6778	Approved
0.7026	Intermediate Similarity	NPD6777	Approved
0.7026	Intermediate Similarity	NPD6779	Approved
0.7026	Intermediate Similarity	NPD6776	Approved
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2798	Approved
0.7012	Intermediate Similarity	NPD8032	Phase 2
0.7006	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1876	Approved
0.6995	Remote Similarity	NPD7930	Approved
0.6994	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3027	Phase 3
0.6977	Remote Similarity	NPD7390	Discontinued
0.697	Remote Similarity	NPD8320	Phase 1
0.697	Remote Similarity	NPD8319	Approved
0.6966	Remote Similarity	NPD5977	Approved
0.6966	Remote Similarity	NPD5978	Approved
0.6964	Remote Similarity	NPD6099	Approved
0.6964	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD3267	Approved
0.6951	Remote Similarity	NPD6798	Discontinued
0.695	Remote Similarity	NPD7701	Phase 2
0.694	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7999	Approved
0.6931	Remote Similarity	NPD7801	Approved
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD447	Suspended
0.6927	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5711	Approved
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD5536	Phase 2
0.6923	Remote Similarity	NPD5710	Approved
0.6918	Remote Similarity	NPD1281	Approved
0.6905	Remote Similarity	NPD2799	Discontinued
0.6901	Remote Similarity	NPD8166	Discontinued
0.6901	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4110	Phase 3
0.6897	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6873	Phase 2
0.6875	Remote Similarity	NPD3972	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4288	Approved
0.6871	Remote Similarity	NPD3018	Phase 2
0.6869	Remote Similarity	NPD6823	Phase 2
0.6867	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1613	Approved
0.6867	Remote Similarity	NPD943	Approved
0.6865	Remote Similarity	NPD7799	Discontinued
0.6865	Remote Similarity	NPD7177	Discontinued
0.6864	Remote Similarity	NPD1551	Phase 2
0.6862	Remote Similarity	NPD7549	Discontinued
0.686	Remote Similarity	NPD3887	Approved
0.6853	Remote Similarity	NPD4107	Approved
0.6848	Remote Similarity	NPD3268	Approved
0.6837	Remote Similarity	NPD7700	Phase 2
0.6837	Remote Similarity	NPD7699	Phase 2

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