NPASS Compound

Structure

CID326144 OpenBabel06191716182D 37 40 0 0 1 0 0 0 0 0999 V2000 -5.7345 -1.6111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5456 -2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3699 -0.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3883 -3.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1812 3.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8002 2.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3716 2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9058 2.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6573 1.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7306 -1.7229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5598 -0.7705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 -1.2467 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1812 -1.9201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4901 -0.5096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4441 -3.5556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1812 0.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5553 -1.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1812 2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9058 -1.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2288 0.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5553 -0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8546 -0.2943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2288 -1.9201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2288 2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9058 -0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7526 1.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7306 0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3657 -1.4538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0796 -4.4355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6573 2.8535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7526 2.8535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8478 1.2039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7306 2.0867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7345 0.0702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8643 -2.8000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 34 1 0 0 0 0 11 35 1 0 0 0 0 12 1 1 6 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 2 1 6 0 0 0 13 23 1 0 0 0 0 14 28 2 0 0 0 0 14 36 1 0 0 0 0 15 29 2 0 0 0 0 15 37 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 2 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 22 36 1 1 0 0 0 23 37 1 6 0 0 0 24 26 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.2
Volume:	508.133
LogP:	3.143
LogD:	2.994
LogS:	-4.153
# Rotatable Bonds:	8
TPSA:	107.98
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	4.137
Fsp3:	0.481
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:	-4.812
MDCK Permeability:	3.233608367736451e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.218
Plasma Protein Binding (PPB):	75.92123413085938%
Volume Distribution (VD):	0.974
Pgp-substrate:	13.888418197631836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.83
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.56
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	1.897
Half-life (T1/2):	0.154

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.034
Carcinogencity:	0.07
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.122

Download Data

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

Natural Product: NPC326144

Natural Product ID:	NPC326144
*Common Name:**	Ananolignan F
IUPAC Name:	n.a.
Synonyms:	Ananolignan F
Standard InCHIKey:	JFBLYFBBLCKNMR-LPWDXZGXSA-N
Standard InCHI:	InChI=1S/C27H32O10/c1-12-13(2)23(37-15(4)29)17-10-19-25(35-11-34-19)27(33-8)21(17)20-16(22(12)36-14(3)28)9-18(30-5)24(31-6)26(20)32-7/h9-10,12-13,22-23H,11H2,1-8H3/t12-,13+,22+,23+/m0/s1
SMILES:	CC1C(C(C2=CC(=C(C(=C2C3=C(C4=C(C=C3C1OC(=O)C)OCO4)OC)OC)OC)OC)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782114
PubChem CID:	53262900
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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	90.0	%	PMID[568946]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	88.6	%	PMID[568946]

☑ 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 NPC326144 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	391
0.1-0.2	1568
0.2-0.3	4004
0.3-0.4	10259
0.4-0.5	8465
0.5-0.6	4508
0.6-0.7	8891
0.7-0.8	3898
0.8-0.85	461
0.85-0.9	175
0.9-0.95	59
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC327651
0.9927	High Similarity	NPC318286
0.9926	High Similarity	NPC218510
0.9926	High Similarity	NPC76415
0.9855	High Similarity	NPC321696
0.9855	High Similarity	NPC321958
0.9714	High Similarity	NPC252281
0.9714	High Similarity	NPC477375
0.9714	High Similarity	NPC327352
0.9714	High Similarity	NPC198129
0.9645	High Similarity	NPC477376
0.9645	High Similarity	NPC322426
0.9645	High Similarity	NPC477374
0.9577	High Similarity	NPC316989
0.9574	High Similarity	NPC316676
0.9574	High Similarity	NPC325720
0.9559	High Similarity	NPC865
0.951	High Similarity	NPC224472
0.9507	High Similarity	NPC85141
0.9444	High Similarity	NPC477378
0.9444	High Similarity	NPC475229
0.9444	High Similarity	NPC471154
0.9441	High Similarity	NPC473989
0.9379	High Similarity	NPC477377
0.9379	High Similarity	NPC217708
0.9379	High Similarity	NPC308739
0.9379	High Similarity	NPC474606
0.9379	High Similarity	NPC126405
0.9379	High Similarity	NPC53669
0.9379	High Similarity	NPC297271
0.9379	High Similarity	NPC24562
0.9379	High Similarity	NPC16791
0.9379	High Similarity	NPC77237
0.9375	High Similarity	NPC475756
0.9375	High Similarity	NPC303519
0.9343	High Similarity	NPC143895
0.9338	High Similarity	NPC145722
0.9338	High Similarity	NPC185680
0.9338	High Similarity	NPC256776
0.9315	High Similarity	NPC473425
0.9252	High Similarity	NPC476065
0.9252	High Similarity	NPC238834
0.922	High Similarity	NPC324962
0.9203	High Similarity	NPC11453
0.9203	High Similarity	NPC32189
0.9189	High Similarity	NPC473323
0.9189	High Similarity	NPC477380
0.9189	High Similarity	NPC29727
0.9184	High Similarity	NPC198461
0.9184	High Similarity	NPC348849
0.9184	High Similarity	NPC312763
0.9184	High Similarity	NPC178195
0.9149	High Similarity	NPC230538
0.9149	High Similarity	NPC103637
0.9149	High Similarity	NPC36531
0.9149	High Similarity	NPC229172
0.9143	High Similarity	NPC216434
0.9143	High Similarity	NPC103448
0.9128	High Similarity	NPC477885
0.9128	High Similarity	NPC475592
0.9118	High Similarity	NPC141493
0.9118	High Similarity	NPC184928
0.9116	High Similarity	NPC474514
0.9091	High Similarity	NPC475868
0.9071	High Similarity	NPC201404
0.9071	High Similarity	NPC290714
0.9071	High Similarity	NPC53722
0.9067	High Similarity	NPC215400
0.9067	High Similarity	NPC230531
0.9028	High Similarity	NPC474054
0.9021	High Similarity	NPC121661
0.9021	High Similarity	NPC87883
0.9021	High Similarity	NPC172171
0.9021	High Similarity	NPC239254
0.9021	High Similarity	NPC73467
0.9014	High Similarity	NPC287124
0.9014	High Similarity	NPC474295
0.9007	High Similarity	NPC63061
0.8966	High Similarity	NPC295297
0.8958	High Similarity	NPC189239
0.8958	High Similarity	NPC166506
0.8958	High Similarity	NPC110763
0.8958	High Similarity	NPC197352
0.8947	High Similarity	NPC319749
0.894	High Similarity	NPC325122
0.8913	High Similarity	NPC72046
0.8913	High Similarity	NPC475856
0.8913	High Similarity	NPC65183
0.8913	High Similarity	NPC261812
0.8912	High Similarity	NPC24425
0.8904	High Similarity	NPC477879
0.8897	High Similarity	NPC252286
0.8897	High Similarity	NPC207702
0.8897	High Similarity	NPC149008
0.8897	High Similarity	NPC154971
0.8897	High Similarity	NPC283114
0.8889	High Similarity	NPC141569
0.8889	High Similarity	NPC18211
0.8889	High Similarity	NPC166884
0.8889	High Similarity	NPC143092
0.8889	High Similarity	NPC474036
0.8889	High Similarity	NPC477701
0.8881	High Similarity	NPC133934
0.8881	High Similarity	NPC184641
0.8881	High Similarity	NPC184684
0.8865	High Similarity	NPC196420
0.8857	High Similarity	NPC148893
0.8857	High Similarity	NPC49235
0.8857	High Similarity	NPC25333
0.8851	High Similarity	NPC13985
0.8851	High Similarity	NPC210642
0.8849	High Similarity	NPC1474
0.8849	High Similarity	NPC266848
0.8849	High Similarity	NPC136750
0.8844	High Similarity	NPC474347
0.8844	High Similarity	NPC474393
0.8828	High Similarity	NPC477702
0.8824	High Similarity	NPC258322
0.8824	High Similarity	NPC191352
0.8811	High Similarity	NPC312199
0.88	High Similarity	NPC273578
0.8794	High Similarity	NPC121651
0.8792	High Similarity	NPC302610
0.8786	High Similarity	NPC31530
0.8784	High Similarity	NPC149505
0.8784	High Similarity	NPC477381
0.8784	High Similarity	NPC470916
0.8777	High Similarity	NPC7744
0.8776	High Similarity	NPC304821
0.8774	High Similarity	NPC477884
0.8768	High Similarity	NPC470624
0.8768	High Similarity	NPC237169
0.8767	High Similarity	NPC212890
0.8766	High Similarity	NPC280778
0.875	High Similarity	NPC151423
0.875	High Similarity	NPC9891
0.875	High Similarity	NPC88297
0.875	High Similarity	NPC40237
0.875	High Similarity	NPC186845
0.8742	High Similarity	NPC117154
0.8732	High Similarity	NPC261714
0.8725	High Similarity	NPC477379
0.8723	High Similarity	NPC189474
0.8723	High Similarity	NPC474139
0.8723	High Similarity	NPC236522
0.8718	High Similarity	NPC118162
0.8718	High Similarity	NPC320471
0.8718	High Similarity	NPC83049
0.8707	High Similarity	NPC183083
0.8707	High Similarity	NPC137352
0.8705	High Similarity	NPC192255
0.8671	High Similarity	NPC113550
0.8671	High Similarity	NPC471183
0.8643	High Similarity	NPC102256
0.8639	High Similarity	NPC87295
0.8633	High Similarity	NPC79184
0.8633	High Similarity	NPC307042
0.8633	High Similarity	NPC476399
0.863	High Similarity	NPC92693
0.863	High Similarity	NPC475000
0.863	High Similarity	NPC218841
0.8627	High Similarity	NPC207584
0.8627	High Similarity	NPC19947
0.8623	High Similarity	NPC328682
0.8623	High Similarity	NPC281864
0.8623	High Similarity	NPC54321
0.8621	High Similarity	NPC80326
0.8621	High Similarity	NPC210354
0.8621	High Similarity	NPC176586
0.8621	High Similarity	NPC472562
0.8613	High Similarity	NPC112571
0.8613	High Similarity	NPC50683
0.8613	High Similarity	NPC285725
0.8611	High Similarity	NPC46591
0.8609	High Similarity	NPC149735
0.8609	High Similarity	NPC245948
0.8609	High Similarity	NPC475141
0.8601	High Similarity	NPC283949
0.8592	High Similarity	NPC224941
0.8592	High Similarity	NPC44245
0.8592	High Similarity	NPC311430
0.8592	High Similarity	NPC150534
0.8592	High Similarity	NPC72796
0.8582	High Similarity	NPC196937
0.8581	High Similarity	NPC101755
0.8581	High Similarity	NPC304687
0.8581	High Similarity	NPC80230
0.8581	High Similarity	NPC65574
0.8581	High Similarity	NPC104024
0.8562	High Similarity	NPC474288
0.8562	High Similarity	NPC32373
0.8562	High Similarity	NPC237946
0.8561	High Similarity	NPC476748
0.8553	High Similarity	NPC477883
0.8553	High Similarity	NPC473736
0.8552	High Similarity	NPC300798
0.8552	High Similarity	NPC58137
0.8551	High Similarity	NPC473092
0.8551	High Similarity	NPC8050
0.8551	High Similarity	NPC473093

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 NPC326144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	934
0.2-0.3	1912
0.3-0.4	2780
0.4-0.5	1643
0.5-0.6	944
0.6-0.7	526
0.7-0.8	87
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD37	Approved
0.8562	High Similarity	NPD4966	Approved
0.8562	High Similarity	NPD4965	Approved
0.8562	High Similarity	NPD4967	Phase 2
0.8452	Intermediate Similarity	NPD6234	Discontinued
0.8382	Intermediate Similarity	NPD3705	Approved
0.8228	Intermediate Similarity	NPD7199	Phase 2
0.8199	Intermediate Similarity	NPD7228	Approved
0.8125	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7240	Approved
0.7922	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD3027	Phase 3
0.7742	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6674	Discontinued
0.7655	Intermediate Similarity	NPD3018	Phase 2
0.7643	Intermediate Similarity	NPD1653	Approved
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7517	Intermediate Similarity	NPD1613	Approved
0.7517	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7451	Intermediate Similarity	NPD7266	Discontinued
0.7442	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3818	Discontinued
0.7415	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6232	Discontinued
0.74	Intermediate Similarity	NPD4060	Phase 1
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD5494	Approved
0.7386	Intermediate Similarity	NPD2438	Suspended
0.7383	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7338	Intermediate Similarity	NPD5763	Approved
0.7338	Intermediate Similarity	NPD5762	Approved
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7229	Phase 3
0.7299	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD5691	Approved
0.7261	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7472	Approved
0.7248	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD6355	Discontinued
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7174	Intermediate Similarity	NPD7680	Approved
0.7171	Intermediate Similarity	NPD2979	Phase 3
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7161	Intermediate Similarity	NPD3539	Phase 1
0.7153	Intermediate Similarity	NPD1357	Approved
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1934	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD919	Approved
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7123	Intermediate Similarity	NPD1610	Phase 2
0.7123	Intermediate Similarity	NPD1611	Approved
0.7119	Intermediate Similarity	NPD6843	Phase 3
0.7119	Intermediate Similarity	NPD6842	Approved
0.7119	Intermediate Similarity	NPD6841	Approved
0.7115	Intermediate Similarity	NPD3540	Phase 1
0.7114	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7097	Intermediate Similarity	NPD3748	Approved
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7067	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD3926	Phase 2
0.7048	Intermediate Similarity	NPD5353	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7032	Intermediate Similarity	NPD6111	Discontinued
0.7027	Intermediate Similarity	NPD5005	Approved
0.7027	Intermediate Similarity	NPD5006	Approved
0.7019	Intermediate Similarity	NPD2532	Approved
0.7019	Intermediate Similarity	NPD2534	Approved
0.7019	Intermediate Similarity	NPD2533	Approved
0.7018	Intermediate Similarity	NPD4481	Phase 3
0.7014	Intermediate Similarity	NPD5536	Phase 2
0.7013	Intermediate Similarity	NPD3657	Discovery
0.7011	Intermediate Similarity	NPD6797	Phase 2
0.7007	Intermediate Similarity	NPD1091	Approved
0.7007	Intermediate Similarity	NPD1281	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD3787	Discontinued
0.6988	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4108	Discontinued
0.6986	Remote Similarity	NPD4626	Approved
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7685	Pre-registration
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4055	Discovery
0.6959	Remote Similarity	NPD5242	Approved
0.6951	Remote Similarity	NPD4005	Discontinued
0.6948	Remote Similarity	NPD3620	Phase 2
0.6948	Remote Similarity	NPD4140	Approved
0.6948	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD3384	Approved
0.6928	Remote Similarity	NPD3382	Approved
0.6928	Remote Similarity	NPD5109	Approved
0.6928	Remote Similarity	NPD5110	Phase 2
0.6928	Remote Similarity	NPD5111	Phase 2
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3383	Approved
0.6919	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6166	Phase 2
0.6918	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1652	Phase 2
0.6918	Remote Similarity	NPD5585	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5327	Phase 3
0.6913	Remote Similarity	NPD4749	Approved
0.6903	Remote Similarity	NPD5124	Phase 1
0.6903	Remote Similarity	NPD1933	Approved
0.6903	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4420	Approved
0.6901	Remote Similarity	NPD5535	Approved
0.6899	Remote Similarity	NPD1375	Discontinued
0.6892	Remote Similarity	NPD422	Phase 1
0.6886	Remote Similarity	NPD2801	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7466	Approved
0.6875	Remote Similarity	NPD3892	Phase 2
0.6875	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3750	Approved
0.6871	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5089	Approved
0.6867	Remote Similarity	NPD5090	Approved
0.6867	Remote Similarity	NPD1283	Approved
0.6864	Remote Similarity	NPD7075	Discontinued
0.6863	Remote Similarity	NPD7095	Approved
0.6852	Remote Similarity	NPD6799	Approved
0.6849	Remote Similarity	NPD1548	Phase 1
0.6842	Remote Similarity	NPD1247	Approved
0.6835	Remote Similarity	NPD6100	Approved
0.6835	Remote Similarity	NPD2796	Approved
0.6835	Remote Similarity	NPD2531	Phase 2
0.6835	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6798	Discontinued
0.6818	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7296	Approved
0.681	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6599	Discontinued
0.6807	Remote Similarity	NPD7028	Phase 2
0.6803	Remote Similarity	NPD1651	Approved
0.68	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5058	Phase 3
0.679	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4210	Discontinued
0.6786	Remote Similarity	NPD1358	Approved
0.6786	Remote Similarity	NPD4585	Approved
0.6774	Remote Similarity	NPD8032	Phase 2
0.6772	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6386	Approved
0.6766	Remote Similarity	NPD6385	Approved
0.6759	Remote Similarity	NPD7157	Approved
0.6759	Remote Similarity	NPD709	Approved
0.6757	Remote Similarity	NPD5126	Approved
0.6757	Remote Similarity	NPD5125	Phase 3
0.6752	Remote Similarity	NPD6653	Approved
0.6748	Remote Similarity	NPD4357	Discontinued
0.6747	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5402	Approved
0.6744	Remote Similarity	NPD6959	Discontinued
0.6743	Remote Similarity	NPD3751	Discontinued
0.6733	Remote Similarity	NPD1608	Approved
0.673	Remote Similarity	NPD6032	Approved
0.6727	Remote Similarity	NPD920	Approved
0.6726	Remote Similarity	NPD6801	Discontinued
0.6721	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3134	Approved
0.6711	Remote Similarity	NPD3496	Discontinued
0.671	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1243	Approved
0.6708	Remote Similarity	NPD4236	Phase 3
0.6708	Remote Similarity	NPD4237	Approved

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