NPASS Compound

Structure

NPC149735 OpenBabel07101718322D 35 37 0 0 1 0 0 0 0 0999 V2000 -0.5899 -3.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6163 -2.6163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1146 3.9812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5184 3.9812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0951 0.8293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4302 -1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2658 -2.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7978 -1.0687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4834 -3.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4147 2.4726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3081 1.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7120 1.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7228 -2.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2394 3.1266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1644 3.1266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4147 1.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8185 1.5476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9514 0.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5476 0.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2394 0.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1644 0.8935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8185 2.4726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2973 -0.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8935 -0.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4038 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0687 -2.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8449 0.1753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6731 2.8265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1753 -2.4410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4410 0.1753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5367 -1.1329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3723 -2.0264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0957 -1.3081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3081 -1.3081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 13 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 27 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 15 4 1 6 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 28 1 0 0 0 0 19 24 2 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 25 2 0 0 0 0 22 29 1 1 0 0 0 23 25 1 0 0 0 0 23 32 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 30 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.23
Volume:	499.109
LogP:	3.944
LogD:	3.831
LogS:	-4.687
# Rotatable Bonds:	7
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	4.032
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868
MDCK Permeability:	2.2253376300795935e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.074

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	83.61124420166016%
Volume Distribution (VD):	0.782
Pgp-substrate:	22.76687240600586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.501
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.589
CYP2C9-substrate:	0.865
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.498
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	5.427
Half-life (T1/2):	0.284

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.111
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.068
Skin Sensitization:	0.372
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.156
Respiratory Toxicity:	0.448

Download Data

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

Natural Product: NPC149735

Natural Product ID:	NPC149735
*Common Name:**	Schisantherin F
IUPAC Name:	n.a.
Synonyms:	Schisantherin F
Standard InCHIKey:	KFTCQKGLZKQBNY-SEIIMYQLSA-N
Standard InCHI:	InChI=1S/C27H34O8/c1-9-13(2)27(30)35-26-20-16(11-19(31-5)24(26)33-7)10-14(3)15(4)22(29)17-12-18(28)23(32-6)25(34-8)21(17)20/h9,11-12,14-15,22,28-29H,10H2,1-8H3/b13-9-/t14-,15-,22+/m1/s1
SMILES:	C/C=C(/C)C(=O)Oc1c2-c3c(cc(c(c3OC)OC)O)[C@H]([C@H](C)[C@H](C)Cc2cc(c1OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465865
PubChem CID:	44567510
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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	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	>	200000.0	nM	PMID[465819]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	95230.0	nM	PMID[465819]
NPT2	Others	Unspecified		Ratio	=	4.32	n.a.	PMID[465819]

☑ 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 NPC149735 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	334
0.1-0.2	1423
0.2-0.3	3749
0.3-0.4	8954
0.4-0.5	9656
0.5-0.6	3545
0.6-0.7	5864
0.7-0.8	7636
0.8-0.85	1206
0.85-0.9	283
0.9-0.95	41
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC477381
0.9726	High Similarity	NPC477379
0.9724	High Similarity	NPC474347
0.9724	High Similarity	NPC474393
0.9658	High Similarity	NPC470916
0.9521	High Similarity	NPC477879
0.9517	High Similarity	NPC474054
0.9452	High Similarity	NPC183083
0.9452	High Similarity	NPC295297
0.9452	High Similarity	NPC137352
0.9404	High Similarity	NPC473323
0.9379	High Similarity	NPC87883
0.9338	High Similarity	NPC476065
0.9333	High Similarity	NPC475141
0.9272	High Similarity	NPC473736
0.9216	High Similarity	NPC475592
0.9205	High Similarity	NPC24562
0.9145	High Similarity	NPC473425
0.9139	High Similarity	NPC471154
0.9103	High Similarity	NPC249070
0.9079	High Similarity	NPC126405
0.9079	High Similarity	NPC53669
0.9079	High Similarity	NPC308739
0.9079	High Similarity	NPC217708
0.9079	High Similarity	NPC77237
0.9079	High Similarity	NPC474606
0.9079	High Similarity	NPC297271
0.9079	High Similarity	NPC16791
0.9073	High Similarity	NPC475756
0.9034	High Similarity	NPC471183
0.9032	High Similarity	NPC215400
0.9032	High Similarity	NPC230531
0.902	High Similarity	NPC312763
0.9	High Similarity	NPC187398
0.9	High Similarity	NPC476348
0.8981	High Similarity	NPC473445
0.8981	High Similarity	NPC42797
0.8966	High Similarity	NPC156948
0.8966	High Similarity	NPC86605
0.8966	High Similarity	NPC3072
0.8966	High Similarity	NPC865
0.8966	High Similarity	NPC46277
0.8966	High Similarity	NPC301765
0.8961	High Similarity	NPC238834
0.8947	High Similarity	NPC224472
0.8933	High Similarity	NPC476347
0.8933	High Similarity	NPC178129
0.8924	High Similarity	NPC291977
0.8903	High Similarity	NPC469474
0.8897	High Similarity	NPC133025
0.8896	High Similarity	NPC198461
0.8882	High Similarity	NPC294522
0.8882	High Similarity	NPC21184
0.8882	High Similarity	NPC120426
0.8882	High Similarity	NPC205727
0.8874	High Similarity	NPC198129
0.8874	High Similarity	NPC252281
0.8874	High Similarity	NPC477375
0.8874	High Similarity	NPC316676
0.8874	High Similarity	NPC325720
0.8874	High Similarity	NPC327352
0.8816	High Similarity	NPC322426
0.8816	High Similarity	NPC477376
0.8816	High Similarity	NPC176903
0.8816	High Similarity	NPC30688
0.8816	High Similarity	NPC477374
0.88	High Similarity	NPC163898
0.8792	High Similarity	NPC469630
0.879	High Similarity	NPC328122
0.8782	High Similarity	NPC29727
0.8767	High Similarity	NPC471719
0.8759	High Similarity	NPC7515
0.8759	High Similarity	NPC469659
0.8759	High Similarity	NPC56764
0.8759	High Similarity	NPC276026
0.8759	High Similarity	NPC555
0.8759	High Similarity	NPC289258
0.8759	High Similarity	NPC206737
0.8759	High Similarity	NPC188378
0.8758	High Similarity	NPC473989
0.8758	High Similarity	NPC316989
0.875	High Similarity	NPC252402
0.875	High Similarity	NPC473408
0.875	High Similarity	NPC102934
0.8742	High Similarity	NPC40222
0.8742	High Similarity	NPC268515
0.8733	High Similarity	NPC471763
0.8726	High Similarity	NPC125495
0.8725	High Similarity	NPC469564
0.8718	High Similarity	NPC155015
0.8718	High Similarity	NPC142479
0.8716	High Similarity	NPC267291
0.871	High Similarity	NPC470769
0.871	High Similarity	NPC150442
0.8707	High Similarity	NPC105493
0.8699	High Similarity	NPC214853
0.8699	High Similarity	NPC240279
0.8699	High Similarity	NPC55239
0.8699	High Similarity	NPC180602
0.8693	High Similarity	NPC85141
0.8693	High Similarity	NPC106138
0.8693	High Similarity	NPC475250
0.8684	High Similarity	NPC15577
0.8675	High Similarity	NPC318286
0.8675	High Similarity	NPC166506
0.8675	High Similarity	NPC327651
0.8675	High Similarity	NPC110763
0.8675	High Similarity	NPC197352
0.8675	High Similarity	NPC189239
0.8667	High Similarity	NPC110067
0.8667	High Similarity	NPC91492
0.8667	High Similarity	NPC6568
0.8667	High Similarity	NPC7439
0.8667	High Similarity	NPC34245
0.8667	High Similarity	NPC256555
0.8658	High Similarity	NPC311530
0.8654	High Similarity	NPC7178
0.8654	High Similarity	NPC62903
0.8645	High Similarity	NPC176186
0.8645	High Similarity	NPC264875
0.8645	High Similarity	NPC169404
0.8645	High Similarity	NPC53587
0.8645	High Similarity	NPC163598
0.8645	High Similarity	NPC120774
0.8642	High Similarity	NPC311912
0.863	High Similarity	NPC309744
0.863	High Similarity	NPC135127
0.863	High Similarity	NPC111635
0.8627	High Similarity	NPC93924
0.8627	High Similarity	NPC236166
0.8618	High Similarity	NPC205361
0.8618	High Similarity	NPC321958
0.8618	High Similarity	NPC321696
0.8616	High Similarity	NPC63061
0.8616	High Similarity	NPC24627
0.8609	High Similarity	NPC121661
0.8609	High Similarity	NPC73467
0.8609	High Similarity	NPC326144
0.86	High Similarity	NPC131971
0.86	High Similarity	NPC278469
0.86	High Similarity	NPC193722
0.8591	High Similarity	NPC266197
0.8591	High Similarity	NPC109240
0.8591	High Similarity	NPC291101
0.859	High Similarity	NPC477377
0.859	High Similarity	NPC476154
0.859	High Similarity	NPC65591
0.859	High Similarity	NPC178574
0.8589	High Similarity	NPC88557
0.8581	High Similarity	NPC474886
0.8581	High Similarity	NPC126206
0.8571	High Similarity	NPC469475
0.8571	High Similarity	NPC47398
0.8571	High Similarity	NPC234333
0.8571	High Similarity	NPC260898
0.8571	High Similarity	NPC469518
0.8571	High Similarity	NPC113790
0.8562	High Similarity	NPC275125
0.8562	High Similarity	NPC475840
0.8562	High Similarity	NPC170239
0.8562	High Similarity	NPC97937
0.8553	High Similarity	NPC37502
0.8553	High Similarity	NPC40702
0.8553	High Similarity	NPC267627
0.8552	High Similarity	NPC309787
0.8552	High Similarity	NPC184928
0.8552	High Similarity	NPC141493
0.8544	High Similarity	NPC54928
0.8543	High Similarity	NPC76415
0.8543	High Similarity	NPC324962
0.8543	High Similarity	NPC218510
0.8543	High Similarity	NPC138212
0.8535	High Similarity	NPC268484
0.8533	High Similarity	NPC471389
0.8533	High Similarity	NPC83375
0.8533	High Similarity	NPC224876
0.8533	High Similarity	NPC87725
0.8533	High Similarity	NPC263261
0.8533	High Similarity	NPC300611
0.8526	High Similarity	NPC75695
0.8526	High Similarity	NPC272566
0.8526	High Similarity	NPC477378
0.8526	High Similarity	NPC476434
0.8526	High Similarity	NPC475229
0.8523	High Similarity	NPC13067
0.8523	High Similarity	NPC22517
0.8523	High Similarity	NPC114171
0.8523	High Similarity	NPC43500
0.8523	High Similarity	NPC164148
0.8523	High Similarity	NPC6300
0.8523	High Similarity	NPC230124
0.8516	High Similarity	NPC24425
0.8514	High Similarity	NPC16435
0.8514	High Similarity	NPC162659
0.8514	High Similarity	NPC306441
0.8514	High Similarity	NPC234952
0.8514	High Similarity	NPC265433
0.8514	High Similarity	NPC471664
0.8514	High Similarity	NPC472334
0.8514	High Similarity	NPC248727

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 NPC149735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	898
0.2-0.3	1892
0.3-0.4	2676
0.4-0.5	1708
0.5-0.6	947
0.6-0.7	572
0.7-0.8	156
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD1653	Approved
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8288	Intermediate Similarity	NPD3027	Phase 3
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.821	Intermediate Similarity	NPD6234	Discontinued
0.8125	Intermediate Similarity	NPD37	Approved
0.8086	Intermediate Similarity	NPD4967	Phase 2
0.8086	Intermediate Similarity	NPD4965	Approved
0.8086	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD7228	Approved
0.8027	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7973	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7881	Intermediate Similarity	NPD4060	Phase 1
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6232	Discontinued
0.7836	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD7266	Discontinued
0.7805	Intermediate Similarity	NPD3817	Phase 2
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7472	Approved
0.7758	Intermediate Similarity	NPD3882	Suspended
0.7744	Intermediate Similarity	NPD2801	Approved
0.7744	Intermediate Similarity	NPD7819	Suspended
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7679	Intermediate Similarity	NPD8127	Discontinued
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3750	Approved
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD422	Phase 1
0.7616	Intermediate Similarity	NPD4908	Phase 1
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7595	Intermediate Similarity	NPD1652	Phase 2
0.7595	Intermediate Similarity	NPD6674	Discontinued
0.7586	Intermediate Similarity	NPD7251	Discontinued
0.7586	Intermediate Similarity	NPD7240	Approved
0.758	Intermediate Similarity	NPD5762	Approved
0.758	Intermediate Similarity	NPD5763	Approved
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7543	Intermediate Similarity	NPD7549	Discontinued
0.7532	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD6355	Discontinued
0.747	Intermediate Similarity	NPD6801	Discontinued
0.7455	Intermediate Similarity	NPD4380	Phase 2
0.7451	Intermediate Similarity	NPD4625	Phase 3
0.744	Intermediate Similarity	NPD7768	Phase 2
0.7423	Intermediate Similarity	NPD1512	Approved
0.7423	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5494	Approved
0.7407	Intermediate Similarity	NPD6799	Approved
0.7403	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD6959	Discontinued
0.7349	Intermediate Similarity	NPD6599	Discontinued
0.7342	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD6842	Approved
0.7333	Intermediate Similarity	NPD6843	Phase 3
0.7333	Intermediate Similarity	NPD6841	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.732	Intermediate Similarity	NPD2861	Phase 2
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7308	Intermediate Similarity	NPD3620	Phase 2
0.7308	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2797	Approved
0.7296	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7285	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD447	Suspended
0.7258	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7256	Intermediate Similarity	NPD2533	Approved
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5401	Approved
0.7256	Intermediate Similarity	NPD2532	Approved
0.7256	Intermediate Similarity	NPD2534	Approved
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD919	Approved
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7226	Intermediate Similarity	NPD7095	Approved
0.7222	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8455	Phase 2
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6653	Approved
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7205	Intermediate Similarity	NPD1549	Phase 2
0.7202	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7411	Suspended
0.7197	Intermediate Similarity	NPD4140	Approved
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3749	Approved
0.7193	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1551	Phase 2
0.7188	Intermediate Similarity	NPD2935	Discontinued
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD3268	Approved
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6667	Approved
0.7133	Intermediate Similarity	NPD4626	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7126	Intermediate Similarity	NPD3686	Approved
0.7126	Intermediate Similarity	NPD3687	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7108	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD7680	Approved
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7086	Intermediate Similarity	NPD3926	Phase 2
0.7086	Intermediate Similarity	NPD3496	Discontinued
0.7083	Intermediate Similarity	NPD3226	Approved
0.7081	Intermediate Similarity	NPD2438	Suspended
0.7081	Intermediate Similarity	NPD2796	Approved
0.7076	Intermediate Similarity	NPD5353	Approved
0.7076	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7985	Registered
0.7067	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6832	Phase 2
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD1611	Approved
0.7027	Intermediate Similarity	NPD7157	Approved
0.7027	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7019	Intermediate Similarity	NPD1510	Phase 2
0.7013	Intermediate Similarity	NPD3225	Approved
0.7012	Intermediate Similarity	NPD3892	Phase 2
0.7012	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4666	Phase 3
0.7	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD5089	Approved
0.6994	Remote Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD1608	Approved
0.6989	Remote Similarity	NPD5242	Approved
0.6986	Remote Similarity	NPD228	Approved
0.6982	Remote Similarity	NPD4005	Discontinued
0.6982	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1240	Approved
0.6975	Remote Similarity	NPD6032	Approved
0.697	Remote Similarity	NPD2677	Approved
0.6954	Remote Similarity	NPD5709	Phase 3
0.6948	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7843	Approved
0.6937	Remote Similarity	NPD4340	Discontinued
0.6937	Remote Similarity	NPD5735	Approved
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2029	Clinical (unspecified phase)

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