NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	500.24
Volume:	516.405
LogP:	3.951
LogD:	3.734
LogS:	-5.963
# Rotatable Bonds:	8
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	3.928
Fsp3:	0.464
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:	-4.855
MDCK Permeability:	2.260607470816467e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.195

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	77.1664047241211%
Volume Distribution (VD):	0.792
Pgp-substrate:	24.349733352661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.587
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.662
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.682
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	3.253
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.27
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.1
Respiratory Toxicity:	0.258

Download Data

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

Natural Product: NPC477381

Natural Product ID:	NPC477381
*Common Name:**	[(9R,10R,11R)-11-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyl-3-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] (E)-2-methylbut-2-enoate
IUPAC Name:	[(9R,10R,11R)-11-hydroxy-4,5,14,15,16-pentamethoxy-9,10-dimethyl-3-tricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaenyl] (E)-2-methylbut-2-enoate
Synonyms:	Methyl Schisantherin F
Standard InCHIKey:	MTTZZBYDFMAIFV-UONFBJKUSA-N
Standard InCHI:	InChI=1S/C28H36O8/c1-10-14(2)28(30)36-27-21-17(12-19(31-5)25(27)34-8)11-15(3)16(4)23(29)18-13-20(32-6)24(33-7)26(35-9)22(18)21/h10,12-13,15-16,23,29H,11H2,1-9H3/b14-10+/t15-,16-,23-/m1/s1
SMILES:	C/C=C(\C)/C(=O)OC1=C2C(=CC(=C1OC)OC)C[C@H]([C@H]([C@H](C3=CC(=C(C(=C32)OC)OC)OC)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45272636
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]
NPO23565	Kadsura polysperma	Species	Schisandraceae	Eukaryota	stems	Emei County of Sichuan Province, China	2009-AUG	PMID[22329624]
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]
NPO23565	Kadsura polysperma	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	6

Activity Type	# Activity
Cell Line	5
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]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	41.4	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	41	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	50.4	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	53.4	%	PMID[22329624]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15700	nM	PMID[19413342]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	12.7	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 NPC477381 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	330
0.1-0.2	1354
0.2-0.3	3503
0.3-0.4	8222
0.4-0.5	10371
0.5-0.6	3712
0.6-0.7	6186
0.7-0.8	7990
0.8-0.85	879
0.85-0.9	107
0.9-0.95	35
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.993	High Similarity	NPC477379
0.9793	High Similarity	NPC149735
0.972	High Similarity	NPC477879
0.965	High Similarity	NPC137352
0.965	High Similarity	NPC183083
0.9595	High Similarity	NPC473323
0.9517	High Similarity	NPC474393
0.9517	High Similarity	NPC474347
0.9514	High Similarity	NPC295297
0.9452	High Similarity	NPC470916
0.9392	High Similarity	NPC24562
0.9329	High Similarity	NPC473425
0.931	High Similarity	NPC474054
0.9281	High Similarity	NPC249070
0.92	High Similarity	NPC312763
0.9172	High Similarity	NPC87883
0.9155	High Similarity	NPC865
0.9139	High Similarity	NPC476065
0.9133	High Similarity	NPC297271
0.9133	High Similarity	NPC16791
0.9133	High Similarity	NPC126405
0.9133	High Similarity	NPC217708
0.9133	High Similarity	NPC308739
0.9133	High Similarity	NPC475141
0.9133	High Similarity	NPC53669
0.9133	High Similarity	NPC77237
0.9073	High Similarity	NPC473736
0.9054	High Similarity	NPC327352
0.9054	High Similarity	NPC477375
0.9054	High Similarity	NPC252281
0.9054	High Similarity	NPC316676
0.9054	High Similarity	NPC325720
0.9054	High Similarity	NPC198129
0.902	High Similarity	NPC475592
0.9	High Similarity	NPC224472
0.8993	High Similarity	NPC477374
0.8993	High Similarity	NPC322426
0.8993	High Similarity	NPC477376
0.8961	High Similarity	NPC328122
0.8947	High Similarity	NPC198461
0.894	High Similarity	NPC471154
0.8933	High Similarity	NPC316989
0.8933	High Similarity	NPC473989
0.8882	High Similarity	NPC474606
0.8874	High Similarity	NPC475756
0.8867	High Similarity	NPC85141
0.8851	High Similarity	NPC327651
0.8851	High Similarity	NPC318286
0.8839	High Similarity	NPC230531
0.8839	High Similarity	NPC215400
0.8831	High Similarity	NPC29727
0.8828	High Similarity	NPC471183
0.8819	High Similarity	NPC471719
0.8811	High Similarity	NPC309744
0.88	High Similarity	NPC187398
0.88	High Similarity	NPC476348
0.8792	High Similarity	NPC321958
0.8792	High Similarity	NPC321696
0.879	High Similarity	NPC42797
0.879	High Similarity	NPC473445
0.8784	High Similarity	NPC326144
0.8782	High Similarity	NPC63061
0.8766	High Similarity	NPC238834
0.8759	High Similarity	NPC86605
0.8759	High Similarity	NPC3072
0.8759	High Similarity	NPC46277
0.8759	High Similarity	NPC301765
0.8759	High Similarity	NPC156948
0.8758	High Similarity	NPC477377
0.8734	High Similarity	NPC291977
0.8733	High Similarity	NPC15577
0.8733	High Similarity	NPC178129
0.8733	High Similarity	NPC476347
0.8732	High Similarity	NPC141493
0.8732	High Similarity	NPC184928
0.8716	High Similarity	NPC324962
0.8716	High Similarity	NPC76415
0.8716	High Similarity	NPC218510
0.871	High Similarity	NPC469474
0.8699	High Similarity	NPC43500
0.8699	High Similarity	NPC164148
0.8693	High Similarity	NPC477378
0.8693	High Similarity	NPC475229
0.869	High Similarity	NPC133025
0.8684	High Similarity	NPC21184
0.8684	High Similarity	NPC205727
0.8684	High Similarity	NPC120426
0.8684	High Similarity	NPC294522
0.8675	High Similarity	NPC93924
0.8671	High Similarity	NPC102256
0.8671	High Similarity	NPC5423
0.8667	High Similarity	NPC205361
0.8649	High Similarity	NPC229172
0.8649	High Similarity	NPC36531
0.8649	High Similarity	NPC230538
0.8649	High Similarity	NPC103637
0.8636	High Similarity	NPC476154
0.8621	High Similarity	NPC224941
0.8621	High Similarity	NPC311430
0.8618	High Similarity	NPC176903
0.8618	High Similarity	NPC30688
0.86	High Similarity	NPC475868
0.86	High Similarity	NPC163898
0.8591	High Similarity	NPC469630
0.8591	High Similarity	NPC138212
0.859	High Similarity	NPC477380
0.8581	High Similarity	NPC300611
0.8581	High Similarity	NPC178195
0.8581	High Similarity	NPC348849
0.8553	High Similarity	NPC252402
0.8553	High Similarity	NPC473408
0.8553	High Similarity	NPC102934
0.8552	High Similarity	NPC555
0.8552	High Similarity	NPC469659
0.8552	High Similarity	NPC206737
0.8552	High Similarity	NPC188378
0.8552	High Similarity	NPC289258
0.8552	High Similarity	NPC7515
0.8552	High Similarity	NPC56764
0.8552	High Similarity	NPC276026
0.8543	High Similarity	NPC40222
0.8543	High Similarity	NPC268515
0.8542	High Similarity	NPC245120
0.8535	High Similarity	NPC477885
0.8535	High Similarity	NPC125495
0.8533	High Similarity	NPC471763
0.8533	High Similarity	NPC172171
0.8533	High Similarity	NPC239254
0.8531	High Similarity	NPC469612
0.8531	High Similarity	NPC307042
0.8531	High Similarity	NPC476399
0.8531	High Similarity	NPC469614
0.8531	High Similarity	NPC79184
0.8526	High Similarity	NPC155015
0.8526	High Similarity	NPC142479
0.8523	High Similarity	NPC469564
0.8521	High Similarity	NPC149008
0.8521	High Similarity	NPC207702
0.8521	High Similarity	NPC283114
0.8516	High Similarity	NPC470769
0.8516	High Similarity	NPC150442
0.8514	High Similarity	NPC267291
0.8509	High Similarity	NPC118162
0.8509	High Similarity	NPC83049
0.8509	High Similarity	NPC320471
0.8503	High Similarity	NPC131198
0.8503	High Similarity	NPC477938
0.8503	High Similarity	NPC105493
0.8497	Intermediate Similarity	NPC475250
0.8497	Intermediate Similarity	NPC106138
0.8493	Intermediate Similarity	NPC240279
0.8493	Intermediate Similarity	NPC214853
0.8493	Intermediate Similarity	NPC180602
0.8493	Intermediate Similarity	NPC55239
0.8481	Intermediate Similarity	NPC241600
0.8481	Intermediate Similarity	NPC173726
0.8477	Intermediate Similarity	NPC166506
0.8477	Intermediate Similarity	NPC125617
0.8477	Intermediate Similarity	NPC110763
0.8477	Intermediate Similarity	NPC189239
0.8477	Intermediate Similarity	NPC197352
0.8472	Intermediate Similarity	NPC469625
0.8472	Intermediate Similarity	NPC469613
0.8472	Intermediate Similarity	NPC30043
0.8467	Intermediate Similarity	NPC34245
0.8467	Intermediate Similarity	NPC7439
0.8467	Intermediate Similarity	NPC110067
0.8467	Intermediate Similarity	NPC6568
0.8467	Intermediate Similarity	NPC256555
0.8467	Intermediate Similarity	NPC91492
0.8462	Intermediate Similarity	NPC62903
0.8462	Intermediate Similarity	NPC7178
0.8457	Intermediate Similarity	NPC311912
0.8456	Intermediate Similarity	NPC311530
0.8452	Intermediate Similarity	NPC264875
0.8452	Intermediate Similarity	NPC215060
0.8452	Intermediate Similarity	NPC163598
0.8452	Intermediate Similarity	NPC120774
0.8452	Intermediate Similarity	NPC53587
0.8452	Intermediate Similarity	NPC176186
0.8452	Intermediate Similarity	NPC476352
0.8452	Intermediate Similarity	NPC169404
0.8452	Intermediate Similarity	NPC302610
0.8446	Intermediate Similarity	NPC471388
0.8446	Intermediate Similarity	NPC151946
0.8442	Intermediate Similarity	NPC473091
0.8435	Intermediate Similarity	NPC38099
0.8435	Intermediate Similarity	NPC26954
0.8435	Intermediate Similarity	NPC286843
0.8431	Intermediate Similarity	NPC304821
0.8431	Intermediate Similarity	NPC236166
0.8428	Intermediate Similarity	NPC119910
0.8428	Intermediate Similarity	NPC24627
0.8425	Intermediate Similarity	NPC135127
0.8425	Intermediate Similarity	NPC111635
0.8414	Intermediate Similarity	NPC319969
0.8411	Intermediate Similarity	NPC143092
0.8411	Intermediate Similarity	NPC73467
0.8411	Intermediate Similarity	NPC121661
0.8411	Intermediate Similarity	NPC18211

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 NPC477381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	899
0.2-0.3	1816
0.3-0.4	2649
0.4-0.5	1769
0.5-0.6	972
0.6-0.7	584
0.7-0.8	167
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8405	Intermediate Similarity	NPD5844	Phase 1
0.828	Intermediate Similarity	NPD37	Approved
0.8239	Intermediate Similarity	NPD4966	Approved
0.8239	Intermediate Similarity	NPD4965	Approved
0.8239	Intermediate Similarity	NPD4967	Phase 2
0.8141	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8082	Intermediate Similarity	NPD3027	Phase 3
0.8041	Intermediate Similarity	NPD1613	Approved
0.8041	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7199	Phase 2
0.8025	Intermediate Similarity	NPD6234	Discontinued
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.7904	Intermediate Similarity	NPD7228	Approved
0.7888	Intermediate Similarity	NPD7819	Suspended
0.7879	Intermediate Similarity	NPD6232	Discontinued
0.784	Intermediate Similarity	NPD3817	Phase 2
0.7831	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1934	Approved
0.7823	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8127	Discontinued
0.78	Intermediate Similarity	NPD4060	Phase 1
0.7785	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD5124	Phase 1
0.7706	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD3818	Discontinued
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3750	Approved
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7549	Discontinued
0.7669	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD422	Phase 1
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7647	Intermediate Similarity	NPD7054	Approved
0.7636	Intermediate Similarity	NPD7075	Discontinued
0.7628	Intermediate Similarity	NPD6674	Discontinued
0.7628	Intermediate Similarity	NPD1652	Phase 2
0.7616	Intermediate Similarity	NPD7240	Approved
0.7613	Intermediate Similarity	NPD7266	Discontinued
0.7613	Intermediate Similarity	NPD5763	Approved
0.7613	Intermediate Similarity	NPD5762	Approved
0.7602	Intermediate Similarity	NPD7472	Approved
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD3882	Suspended
0.7564	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2801	Approved
0.755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5494	Approved
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD6355	Discontinued
0.7515	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD3748	Approved
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.747	Intermediate Similarity	NPD7768	Phase 2
0.7467	Intermediate Similarity	NPD3018	Phase 2
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.745	Intermediate Similarity	NPD2797	Approved
0.7438	Intermediate Similarity	NPD6799	Approved
0.7434	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7251	Discontinued
0.7414	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5403	Approved
0.7403	Intermediate Similarity	NPD447	Suspended
0.74	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6959	Discontinued
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD919	Approved
0.7378	Intermediate Similarity	NPD6599	Discontinued
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.736	Intermediate Similarity	NPD6842	Approved
0.736	Intermediate Similarity	NPD6843	Phase 3
0.736	Intermediate Similarity	NPD6841	Approved
0.7358	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4110	Phase 3
0.7356	Intermediate Similarity	NPD6797	Phase 2
0.7351	Intermediate Similarity	NPD2861	Phase 2
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD7411	Suspended
0.7333	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1511	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6099	Approved
0.7325	Intermediate Similarity	NPD6100	Approved
0.7321	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3268	Approved
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7315	Intermediate Similarity	NPD2983	Phase 2
0.7315	Intermediate Similarity	NPD2982	Phase 2
0.7315	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6190	Approved
0.7305	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3705	Approved
0.7296	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD2532	Approved
0.7284	Intermediate Similarity	NPD2534	Approved
0.7284	Intermediate Similarity	NPD5401	Approved
0.7284	Intermediate Similarity	NPD2533	Approved
0.7283	Intermediate Similarity	NPD3751	Discontinued
0.7279	Intermediate Similarity	NPD4626	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7267	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD6667	Approved
0.726	Intermediate Similarity	NPD1548	Phase 1
0.7256	Intermediate Similarity	NPD3686	Approved
0.7256	Intermediate Similarity	NPD3687	Approved
0.7255	Intermediate Similarity	NPD7095	Approved
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7246	Intermediate Similarity	NPD8455	Phase 2
0.7244	Intermediate Similarity	NPD6653	Approved
0.7239	Intermediate Similarity	NPD1512	Approved
0.7239	Intermediate Similarity	NPD6273	Approved
0.7233	Intermediate Similarity	NPD1549	Phase 2
0.723	Intermediate Similarity	NPD3496	Discontinued
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD3749	Approved
0.7215	Intermediate Similarity	NPD1551	Phase 2
0.7215	Intermediate Similarity	NPD2796	Approved
0.7215	Intermediate Similarity	NPD2935	Discontinued
0.7215	Intermediate Similarity	NPD2438	Suspended
0.7212	Intermediate Similarity	NPD3226	Approved
0.7211	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD3926	Phase 2
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7207	Intermediate Similarity	NPD8434	Phase 2
0.7202	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7192	Intermediate Similarity	NPD5536	Phase 2
0.719	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1611	Approved
0.7178	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7126	Intermediate Similarity	NPD5090	Approved
0.7126	Intermediate Similarity	NPD5089	Approved
0.7119	Intermediate Similarity	NPD7685	Pre-registration
0.7115	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD4005	Discontinued
0.7108	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6032	Approved
0.7097	Intermediate Similarity	NPD7985	Registered
0.7097	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1091	Approved
0.7063	Intermediate Similarity	NPD6004	Phase 3
0.7063	Intermediate Similarity	NPD6005	Phase 3
0.7063	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD7157	Approved
0.7051	Intermediate Similarity	NPD6233	Phase 2
0.7044	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD1510	Phase 2
0.7039	Intermediate Similarity	NPD1283	Approved
0.7037	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7039	Approved
0.7022	Intermediate Similarity	NPD7038	Approved
0.7019	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD1247	Approved
0.6994	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2677	Approved
0.6993	Remote Similarity	NPD3267	Approved
0.6993	Remote Similarity	NPD3266	Approved
0.6988	Remote Similarity	NPD920	Approved
0.6987	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1296	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