NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	596.26
Volume:	606.636
LogP:	4.446
LogD:	3.974
LogS:	-5.689
# Rotatable Bonds:	10
TPSA:	107.98
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	4.533
Fsp3:	0.455
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:	-4.77
MDCK Permeability:	2.0681942260125652e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	74.740966796875%
Volume Distribution (VD):	0.907
Pgp-substrate:	15.276018142700195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.932
CYP2C9-inhibitor:	0.97
CYP2C9-substrate:	0.695
CYP2D6-inhibitor:	0.373
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.923

ADMET: Excretion

Clearance (CL):	4.058
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.061
Skin Sensitization:	0.098
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.107
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC477376

Natural Product ID:	NPC477376
*Common Name:**	Polysperlignan D
IUPAC Name:	[(8R,9S,10R,11R)-3,4,5,19-tetramethoxy-9,10-dimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaen-11-yl] (E)-2-methylbut-2-enoate
Synonyms:	Polysperlignan D
Standard InCHIKey:	HFXDDWNNHDACFM-KZFNYMMPSA-N
Standard InCHI:	InChI=1S/C33H40O10/c1-11-16(3)32(34)42-26-18(5)19(6)27(43-33(35)17(4)12-2)21-14-23-29(41-15-40-23)31(39-10)25(21)24-20(26)13-22(36-7)28(37-8)30(24)38-9/h11-14,18-19,26-27H,15H2,1-10H3/b16-11-,17-12+/t18-,19+,26+,27+/m0/s1
SMILES:	C/C=C(\C)/C(=O)O[C@@H]1[C@@H]([C@@H]([C@H](C2=CC(=C(C(=C2C3=C(C4=C(C=C13)OCO4)OC)OC)OC)OC)OC(=O)/C(=C\C)/C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57333571
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
NPO23565	Kadsura polysperma	Species	Schisandraceae	Eukaryota	stems	Emei County of Sichuan Province, China	2009-AUG	PMID[22329624]
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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	34.4	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	50	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	50.3	%	PMID[22329624]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	55.8	%	PMID[22329624]

☑ 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 NPC477376 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	387
0.1-0.2	1527
0.2-0.3	3673
0.3-0.4	8989
0.4-0.5	9782
0.5-0.6	3924
0.6-0.7	8806
0.7-0.8	5096
0.8-0.85	345
0.85-0.9	99
0.9-0.95	42
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477374
1.0	High Similarity	NPC322426
0.993	High Similarity	NPC316989
0.9929	High Similarity	NPC252281
0.9929	High Similarity	NPC327352
0.9929	High Similarity	NPC477375
0.9929	High Similarity	NPC198129
0.9724	High Similarity	NPC477377
0.972	High Similarity	NPC85141
0.9716	High Similarity	NPC318286
0.9716	High Similarity	NPC327651
0.9655	High Similarity	NPC477378
0.9655	High Similarity	NPC475229
0.9648	High Similarity	NPC321958
0.9648	High Similarity	NPC321696
0.9645	High Similarity	NPC326144
0.9589	High Similarity	NPC53669
0.9589	High Similarity	NPC16791
0.9589	High Similarity	NPC217708
0.9589	High Similarity	NPC77237
0.9589	High Similarity	NPC126405
0.9589	High Similarity	NPC308739
0.9589	High Similarity	NPC24562
0.9589	High Similarity	NPC297271
0.9574	High Similarity	NPC76415
0.9574	High Similarity	NPC218510
0.9463	High Similarity	NPC477885
0.9463	High Similarity	NPC475592
0.9459	High Similarity	NPC476065
0.9452	High Similarity	NPC224472
0.9396	High Similarity	NPC473323
0.9396	High Similarity	NPC477380
0.9392	High Similarity	NPC198461
0.9392	High Similarity	NPC312763
0.9392	High Similarity	NPC348849
0.9392	High Similarity	NPC178195
0.9276	High Similarity	NPC319749
0.9257	High Similarity	NPC471154
0.9247	High Similarity	NPC316676
0.9247	High Similarity	NPC325720
0.922	High Similarity	NPC865
0.9195	High Similarity	NPC474606
0.9189	High Similarity	NPC303519
0.9189	High Similarity	NPC475756
0.9178	High Similarity	NPC295297
0.9145	High Similarity	NPC215400
0.9145	High Similarity	NPC325122
0.9145	High Similarity	NPC230531
0.9133	High Similarity	NPC473425
0.9122	High Similarity	NPC473989
0.9097	High Similarity	NPC477884
0.9073	High Similarity	NPC238834
0.906	High Similarity	NPC477379
0.9054	High Similarity	NPC474347
0.9054	High Similarity	NPC474393
0.9026	High Similarity	NPC258322
0.9026	High Similarity	NPC191352
0.9014	High Similarity	NPC143895
0.9013	High Similarity	NPC29727
0.9007	High Similarity	NPC256776
0.9007	High Similarity	NPC185680
0.9007	High Similarity	NPC145722
0.8993	High Similarity	NPC477381
0.8993	High Similarity	NPC470916
0.8968	High Similarity	NPC280778
0.8947	High Similarity	NPC117154
0.894	High Similarity	NPC474514
0.8919	High Similarity	NPC137352
0.8919	High Similarity	NPC183083
0.8917	High Similarity	NPC320471
0.8917	High Similarity	NPC83049
0.8917	High Similarity	NPC118162
0.8904	High Similarity	NPC324962
0.8881	High Similarity	NPC11453
0.8881	High Similarity	NPC32189
0.8868	High Similarity	NPC477883
0.8839	High Similarity	NPC63061
0.8836	High Similarity	NPC230538
0.8836	High Similarity	NPC229172
0.8836	High Similarity	NPC36531
0.8836	High Similarity	NPC103637
0.8828	High Similarity	NPC216434
0.8828	High Similarity	NPC103448
0.8816	High Similarity	NPC475141
0.8816	High Similarity	NPC149735
0.8794	High Similarity	NPC184928
0.8794	High Similarity	NPC141493
0.8784	High Similarity	NPC475868
0.8759	High Similarity	NPC290714
0.8759	High Similarity	NPC201404
0.8759	High Similarity	NPC53722
0.8758	High Similarity	NPC473736
0.8758	High Similarity	NPC477881
0.875	High Similarity	NPC220577
0.8742	High Similarity	NPC311912
0.8742	High Similarity	NPC79322
0.8733	High Similarity	NPC477879
0.8726	High Similarity	NPC61141
0.8725	High Similarity	NPC474054
0.8716	High Similarity	NPC172171
0.8716	High Similarity	NPC87883
0.8716	High Similarity	NPC143092
0.8716	High Similarity	NPC475000
0.8716	High Similarity	NPC121661
0.8716	High Similarity	NPC474036
0.8716	High Similarity	NPC18211
0.8716	High Similarity	NPC239254
0.8716	High Similarity	NPC73467
0.8707	High Similarity	NPC474295
0.8707	High Similarity	NPC287124
0.8688	High Similarity	NPC88557
0.8684	High Similarity	NPC210642
0.8684	High Similarity	NPC13985
0.8658	High Similarity	NPC166506
0.8658	High Similarity	NPC110763
0.8658	High Similarity	NPC197352
0.8658	High Similarity	NPC189239
0.8654	High Similarity	NPC173726
0.8654	High Similarity	NPC241600
0.8636	High Similarity	NPC273578
0.8627	High Similarity	NPC104353
0.8618	High Similarity	NPC24425
0.8618	High Similarity	NPC149505
0.8609	High Similarity	NPC304821
0.8609	High Similarity	NPC262804
0.8609	High Similarity	NPC40654
0.8601	High Similarity	NPC65183
0.8601	High Similarity	NPC261812
0.8601	High Similarity	NPC475856
0.8601	High Similarity	NPC72046
0.86	High Similarity	NPC154971
0.86	High Similarity	NPC252286
0.86	High Similarity	NPC193779
0.8598	High Similarity	NPC477880
0.8598	High Similarity	NPC477882
0.8591	High Similarity	NPC166884
0.8591	High Similarity	NPC477701
0.8591	High Similarity	NPC141569
0.8582	High Similarity	NPC283114
0.8582	High Similarity	NPC207702
0.8582	High Similarity	NPC149008
0.8581	High Similarity	NPC151423
0.8581	High Similarity	NPC184684
0.8581	High Similarity	NPC40237
0.8581	High Similarity	NPC184641
0.8581	High Similarity	NPC133934
0.8562	High Similarity	NPC196420
0.8553	High Similarity	NPC469475
0.8553	High Similarity	NPC469518
0.8553	High Similarity	NPC475865
0.8552	High Similarity	NPC148893
0.8552	High Similarity	NPC49235
0.8552	High Similarity	NPC25333
0.8542	High Similarity	NPC1474
0.8542	High Similarity	NPC136750
0.8542	High Similarity	NPC266848
0.8533	High Similarity	NPC474158
0.8533	High Similarity	NPC477702
0.8514	High Similarity	NPC312199
0.8509	High Similarity	NPC471180
0.8506	High Similarity	NPC302610
0.8493	Intermediate Similarity	NPC121651
0.8491	Intermediate Similarity	NPC473445
0.8491	Intermediate Similarity	NPC469512
0.8487	Intermediate Similarity	NPC102934
0.8487	Intermediate Similarity	NPC252402
0.8483	Intermediate Similarity	NPC31530
0.8481	Intermediate Similarity	NPC474770
0.8477	Intermediate Similarity	NPC87295
0.8477	Intermediate Similarity	NPC212890
0.8472	Intermediate Similarity	NPC7744
0.8471	Intermediate Similarity	NPC207584
0.8471	Intermediate Similarity	NPC19947
0.8467	Intermediate Similarity	NPC92693
0.8467	Intermediate Similarity	NPC218841
0.8462	Intermediate Similarity	NPC470624
0.8462	Intermediate Similarity	NPC237169
0.8456	Intermediate Similarity	NPC176586
0.8456	Intermediate Similarity	NPC210354
0.8452	Intermediate Similarity	NPC245948
0.844	Intermediate Similarity	NPC88297
0.844	Intermediate Similarity	NPC186845
0.844	Intermediate Similarity	NPC9891
0.8438	Intermediate Similarity	NPC291977
0.8435	Intermediate Similarity	NPC261714
0.8425	Intermediate Similarity	NPC72796
0.8425	Intermediate Similarity	NPC474139
0.8425	Intermediate Similarity	NPC189474
0.8425	Intermediate Similarity	NPC44245
0.8425	Intermediate Similarity	NPC236522
0.8421	Intermediate Similarity	NPC101755
0.8421	Intermediate Similarity	NPC104024
0.8421	Intermediate Similarity	NPC80230
0.8421	Intermediate Similarity	NPC304687
0.8421	Intermediate Similarity	NPC65574
0.8418	Intermediate Similarity	NPC474043
0.8415	Intermediate Similarity	NPC474568
0.8408	Intermediate Similarity	NPC301897
0.8408	Intermediate Similarity	NPC32373
0.8408	Intermediate Similarity	NPC237946

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 NPC477376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	934
0.2-0.3	1857
0.3-0.4	2772
0.4-0.5	1722
0.5-0.6	960
0.6-0.7	499
0.7-0.8	83
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD37	Approved
0.8408	Intermediate Similarity	NPD4967	Phase 2
0.8408	Intermediate Similarity	NPD4965	Approved
0.8408	Intermediate Similarity	NPD4966	Approved
0.8302	Intermediate Similarity	NPD6234	Discontinued
0.8129	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7199	Phase 2
0.8085	Intermediate Similarity	NPD3705	Approved
0.8061	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7240	Approved
0.7736	Intermediate Similarity	NPD1653	Approved
0.7633	Intermediate Similarity	NPD3818	Discontinued
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5494	Approved
0.7588	Intermediate Similarity	NPD5844	Phase 1
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7473	Discontinued
0.7548	Intermediate Similarity	NPD7266	Discontinued
0.7533	Intermediate Similarity	NPD3027	Phase 3
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD7819	Suspended
0.7455	Intermediate Similarity	NPD3817	Phase 2
0.7452	Intermediate Similarity	NPD6674	Discontinued
0.7442	Intermediate Similarity	NPD7074	Phase 3
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7394	Intermediate Similarity	NPD1465	Phase 2
0.7391	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7054	Approved
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7341	Intermediate Similarity	NPD7472	Approved
0.7337	Intermediate Similarity	NPD8127	Discontinued
0.733	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD5283	Phase 1
0.7321	Intermediate Similarity	NPD919	Approved
0.7314	Intermediate Similarity	NPD7808	Phase 3
0.7308	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2438	Suspended
0.726	Intermediate Similarity	NPD5691	Approved
0.7257	Intermediate Similarity	NPD7685	Pre-registration
0.7255	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3926	Phase 2
0.7248	Intermediate Similarity	NPD2983	Phase 2
0.7248	Intermediate Similarity	NPD2982	Phase 2
0.7246	Intermediate Similarity	NPD5353	Approved
0.7241	Intermediate Similarity	NPD5536	Phase 2
0.7229	Intermediate Similarity	NPD1934	Approved
0.7228	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6842	Approved
0.7207	Intermediate Similarity	NPD6843	Phase 3
0.7207	Intermediate Similarity	NPD6841	Approved
0.7202	Intermediate Similarity	NPD3882	Suspended
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7186	Intermediate Similarity	NPD8455	Phase 2
0.7171	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7680	Approved
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7251	Discontinued
0.7152	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5242	Approved
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2532	Approved
0.7117	Intermediate Similarity	NPD2534	Approved
0.7117	Intermediate Similarity	NPD2533	Approved
0.7115	Intermediate Similarity	NPD1933	Approved
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7112	Intermediate Similarity	NPD5005	Approved
0.7112	Intermediate Similarity	NPD5006	Approved
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD5763	Approved
0.7102	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6797	Phase 2
0.7083	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3750	Approved
0.7081	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7075	Discontinued
0.7055	Intermediate Similarity	NPD6799	Approved
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7044	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1247	Approved
0.7022	Intermediate Similarity	NPD7549	Discontinued
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD6166	Phase 2
0.7011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD7768	Phase 2
0.6995	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4420	Approved
0.6989	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8312	Approved
0.6983	Remote Similarity	NPD8313	Approved
0.6982	Remote Similarity	NPD2801	Approved
0.698	Remote Similarity	NPD4626	Approved
0.6975	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4110	Phase 3
0.6964	Remote Similarity	NPD6386	Approved
0.6964	Remote Similarity	NPD5089	Approved
0.6964	Remote Similarity	NPD5090	Approved
0.6964	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD4357	Discontinued
0.6941	Remote Similarity	NPD5402	Approved
0.6941	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3539	Phase 1
0.6933	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD920	Approved
0.6923	Remote Similarity	NPD6801	Discontinued
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD1243	Approved
0.6913	Remote Similarity	NPD1357	Approved
0.6908	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4380	Phase 2
0.6905	Remote Similarity	NPD7028	Phase 2
0.6903	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD1358	Approved
0.6899	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD5124	Phase 1
0.6897	Remote Similarity	NPD3787	Discontinued
0.6894	Remote Similarity	NPD3540	Phase 1
0.6891	Remote Similarity	NPD8151	Discontinued
0.689	Remote Similarity	NPD7124	Phase 2
0.6887	Remote Similarity	NPD422	Phase 1
0.6887	Remote Similarity	NPD1611	Approved
0.6887	Remote Similarity	NPD1281	Approved
0.6887	Remote Similarity	NPD1610	Phase 2
0.6883	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4585	Approved
0.6871	Remote Similarity	NPD4628	Phase 3
0.6868	Remote Similarity	NPD8434	Phase 2
0.6859	Remote Similarity	NPD4625	Phase 3
0.6845	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2861	Phase 2
0.6839	Remote Similarity	NPD6959	Discontinued
0.6832	Remote Similarity	NPD2935	Discontinued
0.6831	Remote Similarity	NPD3134	Approved
0.6829	Remote Similarity	NPD6190	Approved
0.6826	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD4481	Phase 3
0.6813	Remote Similarity	NPD6111	Discontinued
0.6807	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD642	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5585	Approved
0.6795	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3657	Discovery
0.6788	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1091	Approved
0.6772	Remote Similarity	NPD8032	Phase 2
0.677	Remote Similarity	NPD4108	Discontinued
0.6768	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7411	Suspended
0.6763	Remote Similarity	NPD3749	Approved
0.6763	Remote Similarity	NPD4055	Discovery
0.6755	Remote Similarity	NPD17	Approved
0.6753	Remote Similarity	NPD1283	Approved
0.6752	Remote Similarity	NPD7095	Approved
0.6747	Remote Similarity	NPD1511	Approved
0.6747	Remote Similarity	NPD5297	Approved
0.6746	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4005	Discontinued
0.6746	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3620	Phase 2
0.673	Remote Similarity	NPD4140	Approved
0.673	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2531	Phase 2
0.6728	Remote Similarity	NPD6099	Approved
0.6728	Remote Similarity	NPD6100	Approved
0.6725	Remote Similarity	NPD3384	Approved
0.6725	Remote Similarity	NPD3383	Approved
0.6725	Remote Similarity	NPD3382	Approved
0.6723	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7296	Approved
0.6711	Remote Similarity	NPD3496	Discontinued
0.671	Remote Similarity	NPD3267	Approved
0.671	Remote Similarity	NPD3266	Approved
0.671	Remote Similarity	NPD2797	Approved
0.6709	Remote Similarity	NPD5111	Phase 2
0.6709	Remote Similarity	NPD5109	Approved
0.6709	Remote Similarity	NPD5110	Phase 2
0.6709	Remote Similarity	NPD6798	Discontinued

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