NPASS Compound

Structure

NPC473216 OpenBabel07101718312D 45 48 0 0 1 0 0 0 0 0999 V2000 -5.7844 -4.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3558 3.9184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -4.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3558 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5074 -3.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3406 1.1998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2905 -3.7911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3354 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2946 -3.6559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2041 3.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5827 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7343 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5827 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8860 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7343 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8252 -2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8456 -2.8075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6591 -1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3558 0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2041 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3150 -3.6559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2041 2.4490 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5074 -2.4490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6851 1.9278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9878 -2.8595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8860 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2041 0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5074 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3558 -0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6591 -0.9796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0525 1.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5758 0.7925 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.5758 -0.7925 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.3558 -1.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5074 -0.4898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9878 2.8595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6433 -2.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9008 2.4490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 -1.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2731 1.7242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 -2.6558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0525 0.9796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1893 -0.4898 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 1 9 2 0 0 0 0 2 10 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 26 2 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 35 1 0 0 0 0 18 23 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 19 28 2 0 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 22 31 1 0 0 0 0 23 35 1 1 0 0 0 24 37 2 0 0 0 0 24 41 1 0 0 0 0 25 38 2 0 0 0 0 25 42 1 0 0 0 0 26 32 1 0 0 0 0 27 43 1 1 0 0 0 28 33 1 0 0 0 0 29 35 1 6 0 0 0 29 36 1 0 0 0 0 30 36 1 1 0 0 0 30 44 1 0 0 0 0 31 39 2 0 0 0 0 31 43 1 0 0 0 0 32 40 2 0 0 0 0 32 44 1 0 0 0 0 33 41 1 0 0 0 0 33 45 1 0 0 0 0 34 36 1 0 0 0 0 34 42 1 0 0 0 0 34 45 1 0 0 0 0 35 8 1 6 0 0 0 36 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.31
Volume:	649.734
LogP:	4.831
LogD:	3.78
LogS:	-4.934
# Rotatable Bonds:	14
TPSA:	114.43
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	5.687
Fsp3:	0.556
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:	-4.863
MDCK Permeability:	0.0001040189599734731
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	95.7132339477539%
Volume Distribution (VD):	3.236
Pgp-substrate:	4.666935920715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.369
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	3.931
Half-life (T1/2):	0.034

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.704
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.402
Carcinogencity:	0.464
Eye Corrosion:	0.005
Eye Irritation:	0.048
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC473216

Natural Product ID:	NPC473216
*Common Name:**	[(5R,6As,7R,8R,10S,10As)-1,3-Diacetyloxy-7,8-Dimethyl-5-(2-Methylbutanoyloxy)-7-[(2E)-3-Methylpenta-2,4-Dienyl]-1,3,5,6,6A,8,9,10-Octahydrobenzo[D][2]Benzofuran-10-Yl] Benzoate
IUPAC Name:	[(5R,6aS,7R,8R,10S,10aS)-1,3-diacetyloxy-7,8-dimethyl-5-(2-methylbutanoyloxy)-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-10-yl] benzoate
Synonyms:
Standard InCHIKey:	FLLKSIKUPUMYAK-LCXPLBHPSA-N
Standard InCHI:	InChI=1S/C36H46O9/c1-9-21(3)16-17-35(8)23(5)18-30(44-32(40)26-14-12-11-13-15-26)36-28(33(41-24(6)37)45-34(36)42-25(7)38)19-27(20-29(35)36)43-31(39)22(4)10-2/h9,11-16,19,22-23,27,29-30,33-34H,1,10,17-18,20H2,2-8H3/b21-16+/t22?,23-,27+,29+,30+,33?,34?,35-,36-/m1/s1
SMILES:	C=C/C(=C/C[C@]1(C)[C@H](C)C[C@@H]([C@@]23[C@H]1C[C@@H](OC(=O)C(CC)C)C=C3C(OC2OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL372757
PubChem CID:	44404750
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO1241	Laetia procera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16168652]
NPO1241	Laetia procera	Species	Salicaceae	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	6

Activity Type	# Activity
Cell Line	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	27.3	uM	PMID[545606]
NPT83	Cell Line	MCF7	Homo sapiens	Ratio	=	4.6	n.a.	PMID[545606]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	4.66	uM	PMID[545606]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	5.35	uM	PMID[545606]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	>	200.0	uM	PMID[545606]

☑ 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 NPC473216 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	308
0.1-0.2	1200
0.2-0.3	2163
0.3-0.4	4720
0.4-0.5	9356
0.5-0.6	13850
0.6-0.7	9303
0.7-0.8	1525
0.8-0.85	186
0.85-0.9	82
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473399
0.9154	High Similarity	NPC147561
0.8971	High Similarity	NPC475400
0.8955	High Similarity	NPC472577
0.8955	High Similarity	NPC291638
0.8955	High Similarity	NPC195647
0.8955	High Similarity	NPC17877
0.8955	High Similarity	NPC66761
0.8944	High Similarity	NPC162569
0.8944	High Similarity	NPC35160
0.8881	High Similarity	NPC474608
0.8872	High Similarity	NPC471880
0.8872	High Similarity	NPC472394
0.8846	High Similarity	NPC470818
0.8832	High Similarity	NPC183270
0.8832	High Similarity	NPC200592
0.8832	High Similarity	NPC476094
0.8832	High Similarity	NPC477904
0.8832	High Similarity	NPC473613
0.8832	High Similarity	NPC473081
0.8832	High Similarity	NPC473085
0.8832	High Similarity	NPC147880
0.8832	High Similarity	NPC473060
0.8832	High Similarity	NPC473109
0.8832	High Similarity	NPC4341
0.8832	High Similarity	NPC473112
0.8832	High Similarity	NPC48017
0.8832	High Similarity	NPC43241
0.8832	High Similarity	NPC184747
0.8832	High Similarity	NPC473758
0.8832	High Similarity	NPC211137
0.8824	High Similarity	NPC475373
0.8811	High Similarity	NPC116292
0.8811	High Similarity	NPC87630
0.8811	High Similarity	NPC179128
0.8811	High Similarity	NPC267469
0.8803	High Similarity	NPC469448
0.8768	High Similarity	NPC16912
0.8759	High Similarity	NPC210591
0.8759	High Similarity	NPC475652
0.8759	High Similarity	NPC214550
0.875	High Similarity	NPC472372
0.875	High Similarity	NPC472374
0.875	High Similarity	NPC472658
0.875	High Similarity	NPC472657
0.874	High Similarity	NPC470814
0.8712	High Similarity	NPC230331
0.8696	High Similarity	NPC90614
0.8696	High Similarity	NPC472547
0.8696	High Similarity	NPC97667
0.8696	High Similarity	NPC171207
0.8686	High Similarity	NPC283375
0.8686	High Similarity	NPC183122
0.8662	High Similarity	NPC208293
0.8643	High Similarity	NPC246480
0.8643	High Similarity	NPC147217
0.8643	High Similarity	NPC473673
0.8643	High Similarity	NPC270498
0.8643	High Similarity	NPC191082
0.8643	High Similarity	NPC177340
0.8643	High Similarity	NPC475429
0.8643	High Similarity	NPC139067
0.8633	High Similarity	NPC41481
0.8633	High Similarity	NPC87448
0.8633	High Similarity	NPC97947
0.8633	High Similarity	NPC118080
0.8633	High Similarity	NPC472576
0.8633	High Similarity	NPC291599
0.8633	High Similarity	NPC27377
0.8613	High Similarity	NPC472545
0.8613	High Similarity	NPC472551
0.8611	High Similarity	NPC469415
0.8603	High Similarity	NPC48929
0.8593	High Similarity	NPC238370
0.8592	High Similarity	NPC474935
0.8582	High Similarity	NPC125106
0.8582	High Similarity	NPC476974
0.8582	High Similarity	NPC57628
0.8582	High Similarity	NPC95265
0.8582	High Similarity	NPC95810
0.8582	High Similarity	NPC472570
0.8582	High Similarity	NPC470231
0.8582	High Similarity	NPC51314
0.8582	High Similarity	NPC67777
0.8582	High Similarity	NPC472573
0.8582	High Similarity	NPC11685
0.8582	High Similarity	NPC188865
0.8582	High Similarity	NPC25768
0.8582	High Similarity	NPC163719
0.8582	High Similarity	NPC472569
0.8582	High Similarity	NPC70716
0.8571	High Similarity	NPC472546
0.8571	High Similarity	NPC34012
0.8562	High Similarity	NPC469422
0.8562	High Similarity	NPC34066
0.8561	High Similarity	NPC470816
0.8561	High Similarity	NPC100913
0.8561	High Similarity	NPC275592
0.8551	High Similarity	NPC39549
0.8542	High Similarity	NPC303429
0.8542	High Similarity	NPC222102
0.8521	High Similarity	NPC470159
0.8521	High Similarity	NPC472568
0.8521	High Similarity	NPC171525
0.8521	High Similarity	NPC158663
0.8521	High Similarity	NPC472575
0.8521	High Similarity	NPC469349
0.8521	High Similarity	NPC472571
0.8521	High Similarity	NPC470157
0.8521	High Similarity	NPC96903
0.8521	High Similarity	NPC471104
0.8521	High Similarity	NPC70403
0.8521	High Similarity	NPC200471
0.8521	High Similarity	NPC476973
0.8521	High Similarity	NPC472572
0.8521	High Similarity	NPC184817
0.8521	High Similarity	NPC177940
0.8521	High Similarity	NPC473088
0.8521	High Similarity	NPC174982
0.8521	High Similarity	NPC29704
0.8519	High Similarity	NPC475478
0.8519	High Similarity	NPC470278
0.8514	High Similarity	NPC476784
0.8511	High Similarity	NPC191387
0.8511	High Similarity	NPC131966
0.8511	High Similarity	NPC163087
0.85	High Similarity	NPC224491
0.8493	Intermediate Similarity	NPC133430
0.8493	Intermediate Similarity	NPC469477
0.8489	Intermediate Similarity	NPC472395
0.8489	Intermediate Similarity	NPC472371
0.8462	Intermediate Similarity	NPC469513
0.8462	Intermediate Similarity	NPC50872
0.8456	Intermediate Similarity	NPC475493
0.8456	Intermediate Similarity	NPC477623
0.8451	Intermediate Similarity	NPC475759
0.8451	Intermediate Similarity	NPC470152
0.8451	Intermediate Similarity	NPC241951
0.8451	Intermediate Similarity	NPC475122
0.8446	Intermediate Similarity	NPC469417
0.8435	Intermediate Similarity	NPC469398
0.8433	Intermediate Similarity	NPC195224
0.8421	Intermediate Similarity	NPC275576
0.8411	Intermediate Similarity	NPC329960
0.8411	Intermediate Similarity	NPC150893
0.8411	Intermediate Similarity	NPC295408
0.8409	Intermediate Similarity	NPC470815
0.8403	Intermediate Similarity	NPC281717
0.8392	Intermediate Similarity	NPC471100
0.8392	Intermediate Similarity	NPC472556
0.8392	Intermediate Similarity	NPC471107
0.8389	Intermediate Similarity	NPC469399
0.838	Intermediate Similarity	NPC91703
0.8369	Intermediate Similarity	NPC266374
0.8358	Intermediate Similarity	NPC473220
0.8358	Intermediate Similarity	NPC470753
0.8358	Intermediate Similarity	NPC169913
0.8345	Intermediate Similarity	NPC301556
0.8345	Intermediate Similarity	NPC270590
0.8345	Intermediate Similarity	NPC266265
0.8345	Intermediate Similarity	NPC476975
0.8345	Intermediate Similarity	NPC92293
0.8345	Intermediate Similarity	NPC471101
0.8333	Intermediate Similarity	NPC203486
0.8333	Intermediate Similarity	NPC473602
0.8322	Intermediate Similarity	NPC38696
0.8311	Intermediate Similarity	NPC5115
0.8311	Intermediate Similarity	NPC469456
0.831	Intermediate Similarity	NPC192658
0.831	Intermediate Similarity	NPC475135
0.8299	Intermediate Similarity	NPC472548
0.8298	Intermediate Similarity	NPC87934
0.8298	Intermediate Similarity	NPC162613
0.8288	Intermediate Similarity	NPC254558
0.8288	Intermediate Similarity	NPC475417
0.8288	Intermediate Similarity	NPC475561
0.8288	Intermediate Similarity	NPC470245
0.8288	Intermediate Similarity	NPC473214
0.8288	Intermediate Similarity	NPC476173
0.8286	Intermediate Similarity	NPC327511
0.8286	Intermediate Similarity	NPC205305
0.8284	Intermediate Similarity	NPC100402
0.8284	Intermediate Similarity	NPC9180
0.8284	Intermediate Similarity	NPC473082
0.8284	Intermediate Similarity	NPC470765
0.8276	Intermediate Similarity	NPC320734
0.8273	Intermediate Similarity	NPC477893
0.8271	Intermediate Similarity	NPC469742
0.8261	Intermediate Similarity	NPC472656
0.8252	Intermediate Similarity	NPC477894
0.8248	Intermediate Similarity	NPC472418
0.8248	Intermediate Similarity	NPC72915
0.8244	Intermediate Similarity	NPC473243
0.8243	Intermediate Similarity	NPC471135
0.8239	Intermediate Similarity	NPC77493
0.8231	Intermediate Similarity	NPC470153
0.8231	Intermediate Similarity	NPC51602
0.8227	Intermediate Similarity	NPC121268
0.8227	Intermediate Similarity	NPC53361
0.8227	Intermediate Similarity	NPC9905

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 NPC473216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	771
0.2-0.3	1337
0.3-0.4	2833
0.4-0.5	2332
0.5-0.6	1260
0.6-0.7	335
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8089	Intermediate Similarity	NPD7799	Discontinued
0.8043	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD7236	Approved
0.7812	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7239	Suspended
0.7574	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8407	Phase 2
0.7462	Intermediate Similarity	NPD2182	Approved
0.7455	Intermediate Similarity	NPD8368	Discontinued
0.7447	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7057	Phase 3
0.7296	Intermediate Similarity	NPD7058	Phase 2
0.7292	Intermediate Similarity	NPD7008	Discontinued
0.726	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6858	Approved
0.7239	Intermediate Similarity	NPD7094	Approved
0.7214	Intermediate Similarity	NPD6287	Discontinued
0.7197	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5126	Approved
0.7194	Intermediate Similarity	NPD5125	Phase 3
0.7154	Intermediate Similarity	NPD164	Approved
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7132	Intermediate Similarity	NPD5951	Approved
0.7123	Intermediate Similarity	NPD3764	Approved
0.7115	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1238	Approved
0.7107	Intermediate Similarity	NPD37	Approved
0.7081	Intermediate Similarity	NPD4967	Phase 2
0.7081	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD4966	Approved
0.7075	Intermediate Similarity	NPD7961	Discontinued
0.7063	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD8166	Discontinued
0.7059	Intermediate Similarity	NPD8312	Approved
0.7052	Intermediate Similarity	NPD8361	Approved
0.7052	Intermediate Similarity	NPD8360	Approved
0.7052	Intermediate Similarity	NPD8435	Approved
0.7051	Intermediate Similarity	NPD6273	Approved
0.705	Intermediate Similarity	NPD7741	Discontinued
0.7012	Intermediate Similarity	NPD8127	Discontinued
0.7007	Intermediate Similarity	NPD2629	Approved
0.6994	Remote Similarity	NPD6234	Discontinued
0.6977	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8032	Phase 2
0.6957	Remote Similarity	NPD8455	Phase 2
0.6954	Remote Similarity	NPD3748	Approved
0.695	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6559	Discontinued
0.6918	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7228	Approved
0.689	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6832	Phase 2
0.6863	Remote Similarity	NPD7266	Discontinued
0.6846	Remote Similarity	NPD6663	Approved
0.6846	Remote Similarity	NPD7713	Phase 3
0.6842	Remote Similarity	NPD7685	Pre-registration
0.6839	Remote Similarity	NPD7003	Approved
0.6835	Remote Similarity	NPD4198	Discontinued
0.6815	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5736	Approved
0.68	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD2438	Suspended
0.6796	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2532	Approved
0.6772	Remote Similarity	NPD2534	Approved
0.6772	Remote Similarity	NPD2533	Approved
0.6772	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2067	Discontinued
0.6761	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2346	Discontinued
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5761	Phase 2
0.6748	Remote Similarity	NPD5760	Phase 2
0.6744	Remote Similarity	NPD7240	Approved
0.6735	Remote Similarity	NPD2798	Approved
0.6731	Remote Similarity	NPD3750	Approved
0.6727	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3226	Approved
0.6708	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3818	Discontinued
0.6692	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1930	Approved
0.6692	Remote Similarity	NPD1929	Approved
0.669	Remote Similarity	NPD3972	Approved
0.669	Remote Similarity	NPD9545	Approved
0.6688	Remote Similarity	NPD2796	Approved
0.6688	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD969	Suspended
0.6648	Remote Similarity	NPD8150	Discontinued
0.6647	Remote Similarity	NPD6765	Approved
0.6647	Remote Similarity	NPD5494	Approved
0.6647	Remote Similarity	NPD6764	Approved
0.6646	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6642	Remote Similarity	NPD5909	Discontinued
0.663	Remote Similarity	NPD8485	Approved
0.6627	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD2799	Discontinued
0.6621	Remote Similarity	NPD1281	Approved
0.662	Remote Similarity	NPD7610	Discontinued
0.6618	Remote Similarity	NPD6686	Approved
0.6615	Remote Similarity	NPD1989	Approved
0.6607	Remote Similarity	NPD7199	Phase 2
0.6606	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1876	Approved
0.6597	Remote Similarity	NPD17	Approved
0.6594	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2066	Phase 3
0.6591	Remote Similarity	NPD7798	Approved
0.6589	Remote Similarity	NPD1202	Approved
0.6581	Remote Similarity	NPD5408	Approved
0.6581	Remote Similarity	NPD5404	Approved
0.6581	Remote Similarity	NPD5406	Approved
0.6581	Remote Similarity	NPD5405	Approved
0.6579	Remote Similarity	NPD4307	Phase 2
0.6575	Remote Similarity	NPD6637	Approved
0.6571	Remote Similarity	NPD6010	Discontinued
0.657	Remote Similarity	NPD5844	Phase 1
0.6567	Remote Similarity	NPD6647	Phase 2
0.6565	Remote Similarity	NPD3495	Discontinued
0.6559	Remote Similarity	NPD8319	Approved
0.6559	Remote Similarity	NPD8320	Phase 1
0.6558	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2313	Discontinued
0.655	Remote Similarity	NPD7473	Discontinued
0.6544	Remote Similarity	NPD6685	Approved
0.6536	Remote Similarity	NPD1933	Approved
0.6536	Remote Similarity	NPD6355	Discontinued
0.6536	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7074	Phase 3
0.6529	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5585	Approved
0.6528	Remote Similarity	NPD5691	Approved
0.6528	Remote Similarity	NPD3024	Approved
0.6528	Remote Similarity	NPD3025	Approved
0.6525	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7411	Suspended
0.6519	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7305	Phase 1
0.6512	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7700	Phase 2
0.6503	Remote Similarity	NPD7699	Phase 2
0.6497	Remote Similarity	NPD6785	Approved
0.6497	Remote Similarity	NPD6784	Approved
0.6497	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8462	Phase 1
0.649	Remote Similarity	NPD6039	Approved
0.6486	Remote Similarity	NPD1283	Approved
0.6486	Remote Similarity	NPD2198	Approved
0.6486	Remote Similarity	NPD2199	Approved
0.6485	Remote Similarity	NPD6801	Discontinued
0.6483	Remote Similarity	NPD2932	Approved
0.6481	Remote Similarity	NPD920	Approved
0.6478	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2531	Phase 2
0.6474	Remote Similarity	NPD7054	Approved
0.6471	Remote Similarity	NPD4140	Approved
0.6471	Remote Similarity	NPD6232	Discontinued
0.6467	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1608	Approved
0.6463	Remote Similarity	NPD4380	Phase 2
0.6452	Remote Similarity	NPD7097	Phase 1
0.6447	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3266	Approved
0.6443	Remote Similarity	NPD2797	Approved
0.6443	Remote Similarity	NPD3267	Approved
0.6438	Remote Similarity	NPD3026	Approved
0.6438	Remote Similarity	NPD3023	Approved
0.6437	Remote Similarity	NPD7472	Approved
0.6436	Remote Similarity	NPD7999	Approved
0.6433	Remote Similarity	NPD1471	Phase 3
0.6429	Remote Similarity	NPD6535	Approved
0.6429	Remote Similarity	NPD230	Phase 1
0.6429	Remote Similarity	NPD6534	Approved
0.6424	Remote Similarity	NPD7055	Discontinued
0.642	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7808	Phase 3

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