NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	666.25
Volume:	680.117
LogP:	5.328
LogD:	3.753
LogS:	-5.166
# Rotatable Bonds:	10
TPSA:	118.98
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	4.321
Fsp3:	0.282
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:	-4.879
MDCK Permeability:	3.7118839827599004e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	94.4986801147461%
Volume Distribution (VD):	0.22
Pgp-substrate:	2.732384443283081%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.664
CYP2C9-inhibitor:	0.969
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.315
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	5.715
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.084
Carcinogencity:	0.178
Eye Corrosion:	0.003
Eye Irritation:	0.248
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC477882

Natural Product ID:	NPC477882
*Common Name:**	[(8S,9S,10S,11R)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(E)-3-phenylprop-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:	[(8S,9S,10S,11R)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(E)-3-phenylprop-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 F
Standard InCHIKey:	ZMHHYYIXOWWUKL-VGRRBQHDSA-N
Standard InCHI:	InChI=1S/C39H38O10/c1-22-33(49-38(41)24-15-11-8-12-16-24)26-20-29-35(48-21-47-29)37(46-6)31(26)30-25(19-28(43-3)34(44-4)36(30)45-5)32(39(22,2)42)27(40)18-17-23-13-9-7-10-14-23/h7-20,22,32-33,42H,21H2,1-6H3/b18-17+/t22-,32+,33+,39-/m0/s1
SMILES:	C[C@H]1[C@H](C2=CC3=C(C(=C2C4=C(C(=C(C=C4[C@@H]([C@@]1(C)O)C(=O)/C=C/C5=CC=CC=C5)OC)OC)OC)OC)OCO3)OC(=O)C6=CC=CC=C6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45273540
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	=	51400	nM	PMID[19413342]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	3.9	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 NPC477882 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	385
0.1-0.2	1622
0.2-0.3	3265
0.3-0.4	7853
0.4-0.5	10265
0.5-0.6	4279
0.6-0.7	5317
0.7-0.8	7694
0.8-0.85	1851
0.85-0.9	148
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477880
0.9817	High Similarity	NPC477881
0.9695	High Similarity	NPC477883
0.9451	High Similarity	NPC477884
0.9394	High Similarity	NPC83049
0.9394	High Similarity	NPC320471
0.9394	High Similarity	NPC118162
0.9268	High Similarity	NPC319749
0.9222	High Similarity	NPC79322
0.9172	High Similarity	NPC469506
0.9167	High Similarity	NPC88557
0.9107	High Similarity	NPC311912
0.9096	High Similarity	NPC280778
0.9085	High Similarity	NPC477885
0.9036	High Similarity	NPC191352
0.9036	High Similarity	NPC258322
0.903	High Similarity	NPC325122
0.9024	High Similarity	NPC477380
0.8929	High Similarity	NPC291977
0.8882	High Similarity	NPC471180
0.8869	High Similarity	NPC42797
0.8869	High Similarity	NPC469512
0.8869	High Similarity	NPC473445
0.8869	High Similarity	NPC61141
0.8841	High Similarity	NPC477377
0.8837	High Similarity	NPC178737
0.8817	High Similarity	NPC475865
0.8817	High Similarity	NPC469518
0.8817	High Similarity	NPC469475
0.8802	High Similarity	NPC328122
0.8793	High Similarity	NPC472723
0.878	High Similarity	NPC475229
0.878	High Similarity	NPC477378
0.8779	High Similarity	NPC180768
0.8764	High Similarity	NPC65489
0.8757	High Similarity	NPC231254
0.8757	High Similarity	NPC249070
0.8728	High Similarity	NPC471181
0.8727	High Similarity	NPC308739
0.8727	High Similarity	NPC126405
0.8727	High Similarity	NPC16791
0.8727	High Similarity	NPC53669
0.8727	High Similarity	NPC297271
0.8727	High Similarity	NPC77237
0.8727	High Similarity	NPC217708
0.8722	High Similarity	NPC264302
0.8701	High Similarity	NPC35924
0.8701	High Similarity	NPC199172
0.8693	High Similarity	NPC471030
0.8693	High Similarity	NPC472725
0.8693	High Similarity	NPC472726
0.869	High Similarity	NPC230531
0.869	High Similarity	NPC215400
0.8683	High Similarity	NPC301897
0.8671	High Similarity	NPC476365
0.8667	High Similarity	NPC201814
0.8667	High Similarity	NPC220577
0.8659	High Similarity	NPC316989
0.8659	High Similarity	NPC260521
0.8659	High Similarity	NPC469649
0.8644	High Similarity	NPC469371
0.8639	High Similarity	NPC474770
0.8636	High Similarity	NPC267549
0.8631	High Similarity	NPC475592
0.8614	High Similarity	NPC474514
0.8614	High Similarity	NPC24562
0.8611	High Similarity	NPC240200
0.8611	High Similarity	NPC290289
0.8611	High Similarity	NPC223534
0.8611	High Similarity	NPC158214
0.8606	High Similarity	NPC224472
0.8603	High Similarity	NPC111490
0.8603	High Similarity	NPC261623
0.8598	High Similarity	NPC477374
0.8598	High Similarity	NPC322426
0.8598	High Similarity	NPC477376
0.8596	High Similarity	NPC100425
0.8588	High Similarity	NPC80956
0.8588	High Similarity	NPC239890
0.8588	High Similarity	NPC209411
0.858	High Similarity	NPC67629
0.858	High Similarity	NPC79736
0.858	High Similarity	NPC125713
0.8571	High Similarity	NPC172033
0.8571	High Similarity	NPC474568
0.8571	High Similarity	NPC88560
0.8571	High Similarity	NPC175230
0.8564	High Similarity	NPC472724
0.8564	High Similarity	NPC187632
0.8564	High Similarity	NPC31208
0.8564	High Similarity	NPC472720
0.8564	High Similarity	NPC160543
0.8564	High Similarity	NPC93065
0.8564	High Similarity	NPC472721
0.8564	High Similarity	NPC469652
0.8563	High Similarity	NPC348849
0.8563	High Similarity	NPC198461
0.8563	High Similarity	NPC178195
0.8547	High Similarity	NPC475738
0.8539	High Similarity	NPC8940
0.8539	High Similarity	NPC170203
0.8538	High Similarity	NPC476371
0.8538	High Similarity	NPC476372
0.8537	High Similarity	NPC327352
0.8537	High Similarity	NPC198129
0.8537	High Similarity	NPC477375
0.8537	High Similarity	NPC252281
0.8533	High Similarity	NPC3474
0.8525	High Similarity	NPC476358
0.8516	High Similarity	NPC40078
0.8516	High Similarity	NPC471091
0.8516	High Similarity	NPC97924
0.8514	High Similarity	NPC476370
0.8514	High Similarity	NPC235575
0.8514	High Similarity	NPC261254
0.8514	High Similarity	NPC38438
0.8512	High Similarity	NPC238834
0.8512	High Similarity	NPC476065
0.85	High Similarity	NPC474093
0.85	High Similarity	NPC104910
0.85	High Similarity	NPC469650
0.8497	Intermediate Similarity	NPC474042
0.8497	Intermediate Similarity	NPC174734
0.8494	Intermediate Similarity	NPC62354
0.8492	Intermediate Similarity	NPC293227
0.8492	Intermediate Similarity	NPC473717
0.8492	Intermediate Similarity	NPC475662
0.8492	Intermediate Similarity	NPC473631
0.8492	Intermediate Similarity	NPC150977
0.8492	Intermediate Similarity	NPC473883
0.8488	Intermediate Similarity	NPC45943
0.848	Intermediate Similarity	NPC34376
0.8475	Intermediate Similarity	NPC196771
0.8466	Intermediate Similarity	NPC476374
0.8466	Intermediate Similarity	NPC472993
0.8466	Intermediate Similarity	NPC316539
0.8462	Intermediate Similarity	NPC473323
0.8462	Intermediate Similarity	NPC469474
0.8457	Intermediate Similarity	NPC149011
0.8457	Intermediate Similarity	NPC212748
0.8457	Intermediate Similarity	NPC204937
0.8457	Intermediate Similarity	NPC470272
0.8453	Intermediate Similarity	NPC105591
0.8453	Intermediate Similarity	NPC475179
0.8452	Intermediate Similarity	NPC473736
0.8452	Intermediate Similarity	NPC312763
0.8448	Intermediate Similarity	NPC150131
0.8448	Intermediate Similarity	NPC311389
0.8448	Intermediate Similarity	NPC470271
0.8448	Intermediate Similarity	NPC261411
0.8448	Intermediate Similarity	NPC43918
0.8448	Intermediate Similarity	NPC190204
0.8448	Intermediate Similarity	NPC473818
0.8443	Intermediate Similarity	NPC104353
0.8436	Intermediate Similarity	NPC53680
0.8436	Intermediate Similarity	NPC208797
0.843	Intermediate Similarity	NPC125991
0.843	Intermediate Similarity	NPC414831
0.843	Intermediate Similarity	NPC478199
0.843	Intermediate Similarity	NPC76687
0.8427	Intermediate Similarity	NPC472387
0.8427	Intermediate Similarity	NPC477895
0.8427	Intermediate Similarity	NPC469418
0.8427	Intermediate Similarity	NPC241196
0.8421	Intermediate Similarity	NPC476373
0.8418	Intermediate Similarity	NPC469354
0.8418	Intermediate Similarity	NPC146803
0.8415	Intermediate Similarity	NPC321696
0.8415	Intermediate Similarity	NPC321958
0.8409	Intermediate Similarity	NPC174700
0.8409	Intermediate Similarity	NPC223375
0.8409	Intermediate Similarity	NPC67134
0.8409	Intermediate Similarity	NPC47140
0.8409	Intermediate Similarity	NPC475825
0.8407	Intermediate Similarity	NPC7839
0.8407	Intermediate Similarity	NPC142291
0.8407	Intermediate Similarity	NPC119094
0.8407	Intermediate Similarity	NPC477083
0.8407	Intermediate Similarity	NPC477081
0.8407	Intermediate Similarity	NPC173872
0.84	Intermediate Similarity	NPC216403
0.84	Intermediate Similarity	NPC186100
0.84	Intermediate Similarity	NPC473202
0.84	Intermediate Similarity	NPC61791
0.84	Intermediate Similarity	NPC117911
0.84	Intermediate Similarity	NPC41494
0.84	Intermediate Similarity	NPC476279
0.8398	Intermediate Similarity	NPC221140
0.8398	Intermediate Similarity	NPC475352
0.8398	Intermediate Similarity	NPC229817
0.8398	Intermediate Similarity	NPC475220
0.8398	Intermediate Similarity	NPC473686
0.8393	Intermediate Similarity	NPC35544
0.8393	Intermediate Similarity	NPC104728
0.8393	Intermediate Similarity	NPC474606
0.8393	Intermediate Similarity	NPC68882
0.8393	Intermediate Similarity	NPC308555
0.8393	Intermediate Similarity	NPC475141
0.8391	Intermediate Similarity	NPC175793
0.8391	Intermediate Similarity	NPC113093

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 NPC477882 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	923
0.2-0.3	1727
0.3-0.4	2622
0.4-0.5	1954
0.5-0.6	996
0.6-0.7	408
0.7-0.8	150
0.8-0.85	28
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD6980	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7473	Discontinued
0.8372	Intermediate Similarity	NPD7199	Phase 2
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD3818	Discontinued
0.8324	Intermediate Similarity	NPD6232	Discontinued
0.8295	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD37	Approved
0.8276	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8249	Intermediate Similarity	NPD7074	Phase 3
0.8246	Intermediate Similarity	NPD4965	Approved
0.8246	Intermediate Similarity	NPD4967	Phase 2
0.8246	Intermediate Similarity	NPD4966	Approved
0.8235	Intermediate Similarity	NPD7819	Suspended
0.8192	Intermediate Similarity	NPD7054	Approved
0.8177	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6234	Discontinued
0.8146	Intermediate Similarity	NPD7472	Approved
0.814	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD7808	Phase 3
0.8103	Intermediate Similarity	NPD5494	Approved
0.8081	Intermediate Similarity	NPD3817	Phase 2
0.8054	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7228	Approved
0.8024	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD3749	Approved
0.7989	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD8313	Approved
0.7967	Intermediate Similarity	NPD8312	Approved
0.7965	Intermediate Similarity	NPD1934	Approved
0.7956	Intermediate Similarity	NPD6559	Discontinued
0.7956	Intermediate Similarity	NPD7251	Discontinued
0.7955	Intermediate Similarity	NPD6959	Discontinued
0.7931	Intermediate Similarity	NPD7768	Phase 2
0.7921	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7874	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7240	Approved
0.7857	Intermediate Similarity	NPD7685	Pre-registration
0.7829	Intermediate Similarity	NPD3882	Suspended
0.7816	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD1465	Phase 2
0.7816	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD8151	Discontinued
0.7803	Intermediate Similarity	NPD7411	Suspended
0.779	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7746	Intermediate Similarity	NPD4380	Phase 2
0.7714	Intermediate Similarity	NPD2801	Approved
0.7714	Intermediate Similarity	NPD8455	Phase 2
0.7709	Intermediate Similarity	NPD3787	Discontinued
0.7688	Intermediate Similarity	NPD7458	Discontinued
0.7667	Intermediate Similarity	NPD3926	Phase 2
0.7647	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD919	Approved
0.7637	Intermediate Similarity	NPD3751	Discontinued
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6799	Approved
0.7558	Intermediate Similarity	NPD2532	Approved
0.7558	Intermediate Similarity	NPD2533	Approved
0.7558	Intermediate Similarity	NPD2534	Approved
0.7558	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6801	Discontinued
0.7556	Intermediate Similarity	NPD8127	Discontinued
0.7551	Intermediate Similarity	NPD7435	Discontinued
0.7543	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD3750	Approved
0.7514	Intermediate Similarity	NPD7229	Phase 3
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD1511	Approved
0.7472	Intermediate Similarity	NPD5402	Approved
0.7462	Intermediate Similarity	NPD7697	Approved
0.7462	Intermediate Similarity	NPD7698	Approved
0.7462	Intermediate Similarity	NPD7696	Phase 3
0.744	Intermediate Similarity	NPD3748	Approved
0.744	Intermediate Similarity	NPD1510	Phase 2
0.7414	Intermediate Similarity	NPD1512	Approved
0.7413	Intermediate Similarity	NPD7874	Approved
0.7413	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1549	Phase 2
0.7399	Intermediate Similarity	NPD7390	Discontinued
0.7398	Intermediate Similarity	NPD6776	Approved
0.7398	Intermediate Similarity	NPD6778	Approved
0.7398	Intermediate Similarity	NPD6779	Approved
0.7398	Intermediate Similarity	NPD6780	Approved
0.7398	Intermediate Similarity	NPD6777	Approved
0.7398	Intermediate Similarity	NPD6781	Approved
0.7398	Intermediate Similarity	NPD6782	Approved
0.7376	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7783	Phase 2
0.7374	Intermediate Similarity	NPD7680	Approved
0.7371	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD8150	Discontinued
0.7368	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD1247	Approved
0.7356	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5401	Approved
0.7356	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8320	Phase 1
0.7337	Intermediate Similarity	NPD8319	Approved
0.7313	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD1240	Approved
0.7291	Intermediate Similarity	NPD7801	Approved
0.7289	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3226	Approved
0.7288	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD920	Approved
0.7263	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1933	Approved
0.7259	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5005	Approved
0.7236	Intermediate Similarity	NPD6823	Phase 2
0.7236	Intermediate Similarity	NPD5006	Approved
0.7232	Intermediate Similarity	NPD1653	Approved
0.7225	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4628	Phase 3
0.7225	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD1607	Approved
0.7216	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD7700	Phase 2
0.7208	Intermediate Similarity	NPD7699	Phase 2
0.7193	Intermediate Similarity	NPD5408	Approved
0.7193	Intermediate Similarity	NPD5404	Approved
0.7193	Intermediate Similarity	NPD5406	Approved
0.7193	Intermediate Similarity	NPD2935	Discontinued
0.7193	Intermediate Similarity	NPD5405	Approved
0.7189	Intermediate Similarity	NPD5242	Approved
0.7186	Intermediate Similarity	NPD3764	Approved
0.7184	Intermediate Similarity	NPD7930	Approved
0.7184	Intermediate Similarity	NPD6190	Approved
0.7182	Intermediate Similarity	NPD5353	Approved
0.7168	Intermediate Similarity	NPD1243	Approved
0.7166	Intermediate Similarity	NPD7799	Discontinued
0.716	Intermediate Similarity	NPD230	Phase 1
0.7159	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7266	Discontinued
0.7151	Intermediate Similarity	NPD7028	Phase 2
0.7143	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4420	Approved
0.7113	Intermediate Similarity	NPD4287	Approved
0.7074	Intermediate Similarity	NPD7177	Discontinued
0.7071	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6674	Discontinued
0.7059	Intermediate Similarity	NPD447	Suspended
0.7052	Intermediate Similarity	NPD2346	Discontinued
0.705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2798	Approved
0.7043	Intermediate Similarity	NPD5710	Approved
0.7043	Intermediate Similarity	NPD5711	Approved
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7029	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8166	Discontinued
0.7017	Intermediate Similarity	NPD6385	Approved
0.7017	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD943	Approved
0.6995	Remote Similarity	NPD8407	Phase 2
0.6994	Remote Similarity	NPD1551	Phase 2
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6979	Remote Similarity	NPD7549	Discontinued
0.6977	Remote Similarity	NPD7097	Phase 1
0.6964	Remote Similarity	NPD6832	Phase 2
0.6961	Remote Similarity	NPD7999	Approved
0.6959	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2344	Approved
0.6951	Remote Similarity	NPD3705	Approved
0.6936	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7033	Discontinued
0.6927	Remote Similarity	NPD8368	Discontinued
0.6927	Remote Similarity	NPD7584	Approved
0.6923	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD2438	Suspended
0.6895	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6798	Discontinued
0.6878	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2800	Approved
0.6875	Remote Similarity	NPD5953	Discontinued
0.6872	Remote Similarity	NPD8404	Phase 2
0.6864	Remote Similarity	NPD4908	Phase 1
0.6859	Remote Similarity	NPD7286	Phase 2
0.6853	Remote Similarity	NPD8361	Approved
0.6853	Remote Similarity	NPD8360	Approved
0.6853	Remote Similarity	NPD8435	Approved
0.685	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5760	Phase 2
0.6848	Remote Similarity	NPD5761	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