NPASS Compound

Structure

CID123153 OpenBabel06191715482D 30 33 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 24 1 0 0 0 0 10 28 1 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 26 2 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 18 23 1 0 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 1 0 0 0 21 23 1 1 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 23 24 1 6 0 0 0 24 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.2
Volume:	426.357
LogP:	3.801
LogD:	2.897
LogS:	-4.859
# Rotatable Bonds:	4
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	4.41
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687
MDCK Permeability:	2.6088984668604098e-05
Pgp-inhibitor:	0.702
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	90.8111343383789%
Volume Distribution (VD):	2.31
Pgp-substrate:	14.650875091552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.637
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.386
CYP2C19-substrate:	0.623
CYP2C9-inhibitor:	0.75
CYP2C9-substrate:	0.54
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.518
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	3.96
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.505
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.194
Carcinogencity:	0.568
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC123153

Natural Product ID:	NPC123153
*Common Name:**	Caesaldekarine
IUPAC Name:	[(1S,3R,4aR,11bS)-1-acetyloxy-4a-hydroxy-4,4,7,11b-tetramethyl-2,3,5,6-tetrahydro-1H-naphtho[2,1-f][1]benzofuran-3-yl] acetate
Synonyms:	Caesaldekarine
Standard InCHIKey:	VVJWDPJDEOTQOZ-AWAHEQQVSA-N
Standard InCHI:	InChI=1S/C24H30O6/c1-13-16-7-9-24(27)22(4,5)20(29-14(2)25)12-21(30-15(3)26)23(24,6)18(16)11-19-17(13)8-10-28-19/h8,10-11,20-21,27H,7,9,12H2,1-6H3/t20-,21+,23+,24-/m1/s1
SMILES:	Cc1c2CC[C@]3(C(C)(C)[C@@H](C[C@@H]([C@]3(C)c2cc2c1cco2)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456938
PubChem CID:	10597887
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	seed kernel	n.a.	PMID[15921414]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15921414]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26402	Caesalpinia crista	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4000.0	nM	PMID[533879]

☑ 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 NPC123153 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	345
0.1-0.2	1447
0.2-0.3	2744
0.3-0.4	6527
0.4-0.5	11211
0.5-0.6	5458
0.6-0.7	6371
0.7-0.8	7935
0.8-0.85	611
0.85-0.9	38
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC308156
0.9551	High Similarity	NPC255787
0.9551	High Similarity	NPC291742
0.9542	High Similarity	NPC472299
0.9363	High Similarity	NPC41689
0.9342	High Similarity	NPC10429
0.9216	High Similarity	NPC44606
0.9145	High Similarity	NPC212257
0.9079	High Similarity	NPC95526
0.9067	High Similarity	NPC290038
0.902	High Similarity	NPC472298
0.8947	High Similarity	NPC286038
0.8924	High Similarity	NPC8389
0.8909	High Similarity	NPC472661
0.8889	High Similarity	NPC66991
0.8889	High Similarity	NPC472660
0.8868	High Similarity	NPC79571
0.8854	High Similarity	NPC104736
0.8854	High Similarity	NPC41880
0.8797	High Similarity	NPC194499
0.8797	High Similarity	NPC195954
0.8797	High Similarity	NPC88007
0.8797	High Similarity	NPC304692
0.8797	High Similarity	NPC7059
0.8797	High Similarity	NPC81405
0.8774	High Similarity	NPC228842
0.8757	High Similarity	NPC472663
0.8757	High Similarity	NPC472662
0.8742	High Similarity	NPC263337
0.8742	High Similarity	NPC140952
0.8742	High Similarity	NPC158542
0.8704	High Similarity	NPC277618
0.8688	High Similarity	NPC4950
0.8688	High Similarity	NPC218818
0.8688	High Similarity	NPC239118
0.8662	High Similarity	NPC294511
0.8662	High Similarity	NPC121615
0.8634	High Similarity	NPC68848
0.8634	High Similarity	NPC188649
0.8634	High Similarity	NPC18986
0.8625	High Similarity	NPC474611
0.8598	High Similarity	NPC296558
0.8598	High Similarity	NPC125465
0.859	High Similarity	NPC211625
0.8589	High Similarity	NPC100849
0.8581	High Similarity	NPC71821
0.858	High Similarity	NPC283209
0.858	High Similarity	NPC285567
0.858	High Similarity	NPC288602
0.858	High Similarity	NPC88841
0.8571	High Similarity	NPC477692
0.8571	High Similarity	NPC260152
0.8553	High Similarity	NPC179170
0.8544	High Similarity	NPC149526
0.8544	High Similarity	NPC48671
0.8544	High Similarity	NPC474417
0.8543	High Similarity	NPC202260
0.8528	High Similarity	NPC473022
0.8528	High Similarity	NPC56358
0.8509	High Similarity	NPC272196
0.8509	High Similarity	NPC164110
0.8509	High Similarity	NPC270044
0.8509	High Similarity	NPC246647
0.8509	High Similarity	NPC212967
0.8509	High Similarity	NPC96342
0.8481	Intermediate Similarity	NPC144010
0.8481	Intermediate Similarity	NPC13282
0.8476	Intermediate Similarity	NPC121995
0.8466	Intermediate Similarity	NPC24761
0.8462	Intermediate Similarity	NPC295914
0.8457	Intermediate Similarity	NPC226287
0.8457	Intermediate Similarity	NPC287559
0.8452	Intermediate Similarity	NPC471305
0.8452	Intermediate Similarity	NPC471451
0.8447	Intermediate Similarity	NPC180924
0.8438	Intermediate Similarity	NPC122365
0.8438	Intermediate Similarity	NPC329844
0.8438	Intermediate Similarity	NPC210942
0.8438	Intermediate Similarity	NPC169990
0.8428	Intermediate Similarity	NPC232645
0.8428	Intermediate Similarity	NPC145830
0.8428	Intermediate Similarity	NPC72958
0.8428	Intermediate Similarity	NPC478148
0.8424	Intermediate Similarity	NPC136641
0.8424	Intermediate Similarity	NPC472784
0.8424	Intermediate Similarity	NPC270312
0.8411	Intermediate Similarity	NPC307401
0.8408	Intermediate Similarity	NPC17101
0.8408	Intermediate Similarity	NPC77903
0.8405	Intermediate Similarity	NPC472618
0.8405	Intermediate Similarity	NPC470810
0.8405	Intermediate Similarity	NPC95472
0.8405	Intermediate Similarity	NPC49009
0.8405	Intermediate Similarity	NPC239270
0.8405	Intermediate Similarity	NPC303210
0.8395	Intermediate Similarity	NPC269495
0.8395	Intermediate Similarity	NPC268360
0.8387	Intermediate Similarity	NPC158871
0.8385	Intermediate Similarity	NPC478159
0.8385	Intermediate Similarity	NPC149618
0.8385	Intermediate Similarity	NPC148938
0.8385	Intermediate Similarity	NPC478161
0.8385	Intermediate Similarity	NPC89625
0.8377	Intermediate Similarity	NPC121158
0.8375	Intermediate Similarity	NPC217447
0.8375	Intermediate Similarity	NPC40356
0.8375	Intermediate Similarity	NPC114880
0.8375	Intermediate Similarity	NPC87708
0.8375	Intermediate Similarity	NPC477690
0.8375	Intermediate Similarity	NPC154683
0.8365	Intermediate Similarity	NPC474660
0.8365	Intermediate Similarity	NPC140133
0.8354	Intermediate Similarity	NPC472841
0.8354	Intermediate Similarity	NPC14499
0.8354	Intermediate Similarity	NPC14822
0.8354	Intermediate Similarity	NPC266743
0.8354	Intermediate Similarity	NPC475039
0.8354	Intermediate Similarity	NPC469889
0.8354	Intermediate Similarity	NPC476035
0.8344	Intermediate Similarity	NPC216755
0.8344	Intermediate Similarity	NPC472877
0.8344	Intermediate Similarity	NPC255414
0.8344	Intermediate Similarity	NPC473927
0.8333	Intermediate Similarity	NPC474360
0.8333	Intermediate Similarity	NPC221992
0.8333	Intermediate Similarity	NPC477674
0.8333	Intermediate Similarity	NPC4547
0.8323	Intermediate Similarity	NPC477669
0.8323	Intermediate Similarity	NPC243577
0.8323	Intermediate Similarity	NPC477691
0.8323	Intermediate Similarity	NPC235333
0.8323	Intermediate Similarity	NPC118086
0.8313	Intermediate Similarity	NPC258249
0.8313	Intermediate Similarity	NPC477672
0.8313	Intermediate Similarity	NPC246164
0.8313	Intermediate Similarity	NPC477673
0.8302	Intermediate Similarity	NPC100985
0.8302	Intermediate Similarity	NPC65589
0.8302	Intermediate Similarity	NPC288036
0.8302	Intermediate Similarity	NPC329933
0.8302	Intermediate Similarity	NPC97028
0.8302	Intermediate Similarity	NPC291049
0.8302	Intermediate Similarity	NPC158338
0.8302	Intermediate Similarity	NPC97029
0.8302	Intermediate Similarity	NPC233267
0.8301	Intermediate Similarity	NPC62735
0.8301	Intermediate Similarity	NPC233707
0.8291	Intermediate Similarity	NPC478163
0.8291	Intermediate Similarity	NPC34802
0.8291	Intermediate Similarity	NPC19747
0.8282	Intermediate Similarity	NPC260902
0.8282	Intermediate Similarity	NPC296957
0.8282	Intermediate Similarity	NPC299094
0.8282	Intermediate Similarity	NPC196448
0.8282	Intermediate Similarity	NPC10051
0.828	Intermediate Similarity	NPC62799
0.828	Intermediate Similarity	NPC208584
0.8278	Intermediate Similarity	NPC209858
0.8278	Intermediate Similarity	NPC324117
0.8278	Intermediate Similarity	NPC213122
0.8274	Intermediate Similarity	NPC472619
0.8274	Intermediate Similarity	NPC475641
0.8274	Intermediate Similarity	NPC475237
0.8272	Intermediate Similarity	NPC213936
0.8272	Intermediate Similarity	NPC297531
0.8272	Intermediate Similarity	NPC99199
0.8272	Intermediate Similarity	NPC477687
0.8272	Intermediate Similarity	NPC477671
0.8269	Intermediate Similarity	NPC251865
0.8263	Intermediate Similarity	NPC53640
0.8261	Intermediate Similarity	NPC207624
0.8261	Intermediate Similarity	NPC273483
0.8261	Intermediate Similarity	NPC271681
0.8256	Intermediate Similarity	NPC104682
0.825	Intermediate Similarity	NPC470568
0.825	Intermediate Similarity	NPC473466
0.825	Intermediate Similarity	NPC158866
0.825	Intermediate Similarity	NPC321896
0.825	Intermediate Similarity	NPC191104
0.825	Intermediate Similarity	NPC119929
0.825	Intermediate Similarity	NPC476185
0.8247	Intermediate Similarity	NPC148374
0.8246	Intermediate Similarity	NPC324220
0.8246	Intermediate Similarity	NPC312630
0.8242	Intermediate Similarity	NPC92589
0.8242	Intermediate Similarity	NPC472783
0.8242	Intermediate Similarity	NPC472780
0.8239	Intermediate Similarity	NPC69647
0.8239	Intermediate Similarity	NPC105415
0.8239	Intermediate Similarity	NPC256672
0.8239	Intermediate Similarity	NPC146388
0.8239	Intermediate Similarity	NPC37139
0.8239	Intermediate Similarity	NPC27221
0.8239	Intermediate Similarity	NPC135325
0.8239	Intermediate Similarity	NPC125182
0.8239	Intermediate Similarity	NPC7025
0.8232	Intermediate Similarity	NPC476350
0.8232	Intermediate Similarity	NPC472617
0.8232	Intermediate Similarity	NPC474373
0.8232	Intermediate Similarity	NPC476349

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 NPC123153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	894
0.2-0.3	1537
0.3-0.4	2432
0.4-0.5	2180
0.5-0.6	1142
0.6-0.7	468
0.7-0.8	191
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8312	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8258	Intermediate Similarity	NPD4628	Phase 3
0.8176	Intermediate Similarity	NPD920	Approved
0.8171	Intermediate Similarity	NPD3749	Approved
0.8165	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8113	Intermediate Similarity	NPD6273	Approved
0.8075	Intermediate Similarity	NPD3226	Approved
0.8075	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD7003	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD8434	Phase 2
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7949	Intermediate Similarity	NPD2346	Discontinued
0.7937	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD3750	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD7458	Discontinued
0.7848	Intermediate Similarity	NPD1243	Approved
0.7844	Intermediate Similarity	NPD7075	Discontinued
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7818	Intermediate Similarity	NPD6801	Discontinued
0.7799	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7177	Discontinued
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5761	Phase 2
0.7771	Intermediate Similarity	NPD2796	Approved
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5760	Phase 2
0.7765	Intermediate Similarity	NPD7229	Phase 3
0.7725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7688	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1549	Phase 2
0.7662	Intermediate Similarity	NPD3764	Approved
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7654	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1283	Approved
0.7614	Intermediate Similarity	NPD6764	Approved
0.7614	Intermediate Similarity	NPD6765	Approved
0.761	Intermediate Similarity	NPD2344	Approved
0.761	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2935	Discontinued
0.7527	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD4380	Phase 2
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7484	Intermediate Similarity	NPD1510	Phase 2
0.7484	Intermediate Similarity	NPD4308	Phase 3
0.7483	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD1608	Approved
0.7471	Intermediate Similarity	NPD3882	Suspended
0.7468	Intermediate Similarity	NPD1607	Approved
0.7456	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD2979	Phase 3
0.7452	Intermediate Similarity	NPD4140	Approved
0.7444	Intermediate Similarity	NPD6784	Approved
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6785	Approved
0.7439	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5406	Approved
0.7438	Intermediate Similarity	NPD5405	Approved
0.7438	Intermediate Similarity	NPD5408	Approved
0.7438	Intermediate Similarity	NPD2438	Suspended
0.7438	Intermediate Similarity	NPD5404	Approved
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7418	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1281	Approved
0.7414	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1778	Approved
0.7399	Intermediate Similarity	NPD8127	Discontinued
0.7396	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD3818	Discontinued
0.7384	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.7342	Intermediate Similarity	NPD1240	Approved
0.7342	Intermediate Similarity	NPD4307	Phase 2
0.7333	Intermediate Similarity	NPD5691	Approved
0.7333	Intermediate Similarity	NPD1651	Approved
0.7329	Intermediate Similarity	NPD4476	Approved
0.7329	Intermediate Similarity	NPD4477	Approved
0.7326	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6798	Discontinued
0.7325	Intermediate Similarity	NPD3268	Approved
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7296	Intermediate Similarity	NPD6355	Discontinued
0.7285	Intermediate Similarity	NPD4626	Approved
0.7285	Intermediate Similarity	NPD17	Approved
0.7283	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7095	Approved
0.7257	Intermediate Similarity	NPD6808	Phase 2
0.7251	Intermediate Similarity	NPD8455	Phase 2
0.7251	Intermediate Similarity	NPD2801	Approved
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7229	Intermediate Similarity	NPD1511	Approved
0.7228	Intermediate Similarity	NPD4287	Approved
0.7226	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD2531	Phase 2
0.7209	Intermediate Similarity	NPD5402	Approved
0.7202	Intermediate Similarity	NPD5403	Approved
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7195	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3751	Discontinued
0.7186	Intermediate Similarity	NPD5401	Approved
0.7178	Intermediate Similarity	NPD6005	Phase 3
0.7178	Intermediate Similarity	NPD6004	Phase 3
0.7178	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6002	Phase 3
0.7174	Intermediate Similarity	NPD7693	Approved
0.7169	Intermediate Similarity	NPD7236	Approved
0.7167	Intermediate Similarity	NPD5953	Discontinued
0.7161	Intermediate Similarity	NPD6696	Suspended
0.7159	Intermediate Similarity	NPD3787	Discontinued
0.7158	Intermediate Similarity	NPD4107	Approved
0.7152	Intermediate Similarity	NPD7008	Discontinued
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7151	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1512	Approved
0.7135	Intermediate Similarity	NPD7435	Discontinued
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7111	Intermediate Similarity	NPD7074	Phase 3
0.711	Intermediate Similarity	NPD4288	Approved
0.7108	Intermediate Similarity	NPD3887	Approved
0.7107	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1611	Approved
0.7073	Intermediate Similarity	NPD5763	Approved
0.7073	Intermediate Similarity	NPD5762	Approved
0.707	Intermediate Similarity	NPD2798	Approved
0.7068	Intermediate Similarity	NPD6776	Approved
0.7068	Intermediate Similarity	NPD6780	Approved
0.7068	Intermediate Similarity	NPD6778	Approved
0.7068	Intermediate Similarity	NPD6779	Approved
0.7068	Intermediate Similarity	NPD6781	Approved
0.7068	Intermediate Similarity	NPD6782	Approved
0.7068	Intermediate Similarity	NPD6777	Approved
0.7063	Intermediate Similarity	NPD6233	Phase 2
0.7063	Intermediate Similarity	NPD6663	Approved
0.7059	Intermediate Similarity	NPD7239	Suspended
0.7059	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7054	Approved
0.7051	Intermediate Similarity	NPD1876	Approved
0.7048	Intermediate Similarity	NPD8166	Discontinued
0.7041	Intermediate Similarity	NPD5049	Phase 3
0.7039	Intermediate Similarity	NPD9545	Approved
0.7037	Intermediate Similarity	NPD6651	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