NPASS Compound

Structure

NPC475872 OpenBabel07101719142D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 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 2.5981 3.5000 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 3.4641 3.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 3.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 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 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 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 -3.4641 -0.0000 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 7 29 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 27 2 0 0 0 0 15 30 1 0 0 0 0 16 28 2 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 25 1 6 0 0 0 23 26 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.25
Volume:	463.585
LogP:	5.936
LogD:	3.638
LogS:	-4.503
# Rotatable Bonds:	5
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	4.296
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.039
MDCK Permeability:	1.5471494407393038e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.81
Plasma Protein Binding (PPB):	81.9219741821289%
Volume Distribution (VD):	0.501
Pgp-substrate:	25.834003448486328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.347
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.321
CYP2C9-substrate:	0.29
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	3.453
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.719
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.405
Skin Sensitization:	0.741
Carcinogencity:	0.714
Eye Corrosion:	0.033
Eye Irritation:	0.056
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC475872

Natural Product ID:	NPC475872
*Common Name:**	[(4As,6As,12S,12As,12Bs)-9-Acetyloxy-12-Methoxy-4,4,6A,12B-Tetramethyl-1,2,3,4A,5,6,12,12A-Octahydrobenzo[A]Xanthen-10-Yl] Acetate
IUPAC Name:	[(4aS,6aS,12S,12aS,12bS)-9-acetyloxy-12-methoxy-4,4,6a,12b-tetramethyl-1,2,3,4a,5,6,12,12a-octahydrobenzo[a]xanthen-10-yl] acetate
Synonyms:
Standard InCHIKey:	CCKHCTFPKJBONS-GDKKAJJHSA-N
Standard InCHI:	InChI=1S/C26H36O6/c1-15(27)30-19-13-17-18(14-20(19)31-16(2)28)32-26(6)12-9-21-24(3,4)10-8-11-25(21,5)23(26)22(17)29-7/h13-14,21-23H,8-12H2,1-7H3/t21-,22+,23+,25-,26-/m0/s1
SMILES:	CO[C@@H]1c2cc(OC(=O)C)c(cc2O[C@@]2([C@H]1[C@@]1(C)CCCC([C@@H]1CC2)(C)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517703
PubChem CID:	10765719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.6	ug.mL-1	PMID[547725]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.4	ug.mL-1	PMID[547725]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.2	ug.mL-1	PMID[547725]

☑ 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 NPC475872 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	441
0.1-0.2	1632
0.2-0.3	3632
0.3-0.4	8482
0.4-0.5	10058
0.5-0.6	5070
0.6-0.7	9269
0.7-0.8	3962
0.8-0.85	133
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9143	High Similarity	NPC474530
0.9143	High Similarity	NPC474540
0.9143	High Similarity	NPC474521
0.8966	High Similarity	NPC90645
0.8865	High Similarity	NPC224941
0.8865	High Similarity	NPC311430
0.8836	High Similarity	NPC472457
0.8792	High Similarity	NPC158784
0.8784	High Similarity	NPC212142
0.8777	High Similarity	NPC474617
0.8776	High Similarity	NPC475896
0.8776	High Similarity	NPC471608
0.8741	High Similarity	NPC306365
0.8733	High Similarity	NPC2745
0.8733	High Similarity	NPC302915
0.8707	High Similarity	NPC292256
0.8681	High Similarity	NPC270256
0.8675	High Similarity	NPC157783
0.8675	High Similarity	NPC325860
0.8671	High Similarity	NPC286843
0.8667	High Similarity	NPC195561
0.8662	High Similarity	NPC474478
0.8662	High Similarity	NPC474600
0.8652	High Similarity	NPC319969
0.8643	High Similarity	NPC476399
0.863	High Similarity	NPC323126
0.8611	High Similarity	NPC865
0.8601	High Similarity	NPC234865
0.8561	High Similarity	NPC474670
0.8531	High Similarity	NPC309953
0.8511	High Similarity	NPC307042
0.8511	High Similarity	NPC79184
0.8511	High Similarity	NPC470624
0.8511	High Similarity	NPC237169
0.85	High Similarity	NPC31707
0.85	High Similarity	NPC474616
0.85	High Similarity	NPC474636
0.85	High Similarity	NPC210674
0.8489	Intermediate Similarity	NPC128321
0.8489	Intermediate Similarity	NPC474632
0.8467	Intermediate Similarity	NPC15577
0.8462	Intermediate Similarity	NPC36437
0.8462	Intermediate Similarity	NPC241341
0.8462	Intermediate Similarity	NPC233018
0.8456	Intermediate Similarity	NPC125617
0.8435	Intermediate Similarity	NPC138149
0.8431	Intermediate Similarity	NPC160196
0.8431	Intermediate Similarity	NPC476452
0.8429	Intermediate Similarity	NPC474821
0.8425	Intermediate Similarity	NPC471388
0.8418	Intermediate Similarity	NPC140346
0.8414	Intermediate Similarity	NPC167517
0.8414	Intermediate Similarity	NPC173660
0.8414	Intermediate Similarity	NPC78047
0.8411	Intermediate Similarity	NPC473876
0.8411	Intermediate Similarity	NPC477879
0.8392	Intermediate Similarity	NPC137669
0.8389	Intermediate Similarity	NPC50250
0.8389	Intermediate Similarity	NPC63879
0.8378	Intermediate Similarity	NPC174522
0.8378	Intermediate Similarity	NPC20631
0.8378	Intermediate Similarity	NPC80326
0.8378	Intermediate Similarity	NPC93640
0.8377	Intermediate Similarity	NPC476154
0.8369	Intermediate Similarity	NPC474651
0.8369	Intermediate Similarity	NPC474623
0.8367	Intermediate Similarity	NPC27495
0.8367	Intermediate Similarity	NPC259519
0.8356	Intermediate Similarity	NPC476171
0.8356	Intermediate Similarity	NPC105493
0.8355	Intermediate Similarity	NPC176903
0.8355	Intermediate Similarity	NPC30688
0.8345	Intermediate Similarity	NPC471909
0.8345	Intermediate Similarity	NPC471625
0.8345	Intermediate Similarity	NPC327382
0.8345	Intermediate Similarity	NPC472424
0.8345	Intermediate Similarity	NPC86892
0.8345	Intermediate Similarity	NPC195022
0.8345	Intermediate Similarity	NPC281241
0.8344	Intermediate Similarity	NPC170239
0.8344	Intermediate Similarity	NPC275125
0.8344	Intermediate Similarity	NPC21776
0.8344	Intermediate Similarity	NPC137352
0.8344	Intermediate Similarity	NPC97937
0.8344	Intermediate Similarity	NPC16269
0.8344	Intermediate Similarity	NPC183083
0.8344	Intermediate Similarity	NPC101376
0.8333	Intermediate Similarity	NPC472522
0.8333	Intermediate Similarity	NPC296624
0.8333	Intermediate Similarity	NPC167111
0.8333	Intermediate Similarity	NPC471910
0.8333	Intermediate Similarity	NPC207002
0.8333	Intermediate Similarity	NPC133956
0.8333	Intermediate Similarity	NPC469557
0.8333	Intermediate Similarity	NPC318400
0.8333	Intermediate Similarity	NPC205316
0.8323	Intermediate Similarity	NPC7178
0.8323	Intermediate Similarity	NPC268484
0.8323	Intermediate Similarity	NPC62903
0.8323	Intermediate Similarity	NPC80918
0.8323	Intermediate Similarity	NPC188578
0.8322	Intermediate Similarity	NPC47633
0.8322	Intermediate Similarity	NPC184928
0.8322	Intermediate Similarity	NPC102044
0.8322	Intermediate Similarity	NPC141493
0.8322	Intermediate Similarity	NPC85264
0.8312	Intermediate Similarity	NPC163598
0.8312	Intermediate Similarity	NPC120774
0.8312	Intermediate Similarity	NPC302610
0.8312	Intermediate Similarity	NPC264875
0.8311	Intermediate Similarity	NPC58137
0.8311	Intermediate Similarity	NPC471389
0.8311	Intermediate Similarity	NPC300611
0.8311	Intermediate Similarity	NPC300798
0.8311	Intermediate Similarity	NPC35216
0.8311	Intermediate Similarity	NPC247291
0.8301	Intermediate Similarity	NPC205727
0.8301	Intermediate Similarity	NPC120426
0.8301	Intermediate Similarity	NPC477381
0.8301	Intermediate Similarity	NPC294522
0.8301	Intermediate Similarity	NPC21184
0.8301	Intermediate Similarity	NPC474305
0.8299	Intermediate Similarity	NPC25966
0.8299	Intermediate Similarity	NPC127218
0.8299	Intermediate Similarity	NPC19869
0.8299	Intermediate Similarity	NPC319647
0.8299	Intermediate Similarity	NPC245207
0.8298	Intermediate Similarity	NPC471986
0.8298	Intermediate Similarity	NPC202904
0.8298	Intermediate Similarity	NPC189248
0.8288	Intermediate Similarity	NPC471630
0.8288	Intermediate Similarity	NPC476455
0.8288	Intermediate Similarity	NPC55615
0.8288	Intermediate Similarity	NPC283019
0.8288	Intermediate Similarity	NPC149320
0.8288	Intermediate Similarity	NPC128529
0.8288	Intermediate Similarity	NPC472800
0.8288	Intermediate Similarity	NPC160727
0.8288	Intermediate Similarity	NPC177281
0.8278	Intermediate Similarity	NPC233980
0.8278	Intermediate Similarity	NPC112251
0.8278	Intermediate Similarity	NPC205361
0.8276	Intermediate Similarity	NPC267412
0.8276	Intermediate Similarity	NPC127888
0.8276	Intermediate Similarity	NPC287182
0.8276	Intermediate Similarity	NPC47163
0.8276	Intermediate Similarity	NPC147030
0.8276	Intermediate Similarity	NPC195343
0.8276	Intermediate Similarity	NPC319859
0.8276	Intermediate Similarity	NPC84894
0.8276	Intermediate Similarity	NPC198381
0.8276	Intermediate Similarity	NPC74655
0.8276	Intermediate Similarity	NPC164269
0.8276	Intermediate Similarity	NPC309744
0.8276	Intermediate Similarity	NPC18804
0.8276	Intermediate Similarity	NPC166672
0.8276	Intermediate Similarity	NPC100986
0.8276	Intermediate Similarity	NPC260265
0.8269	Intermediate Similarity	NPC155015
0.8269	Intermediate Similarity	NPC142479
0.8267	Intermediate Similarity	NPC280092
0.8267	Intermediate Similarity	NPC12641
0.8267	Intermediate Similarity	NPC473108
0.8267	Intermediate Similarity	NPC93323
0.8267	Intermediate Similarity	NPC45257
0.8267	Intermediate Similarity	NPC473845
0.8267	Intermediate Similarity	NPC326144
0.8258	Intermediate Similarity	NPC223720
0.8255	Intermediate Similarity	NPC475891
0.8255	Intermediate Similarity	NPC59841
0.8255	Intermediate Similarity	NPC204347
0.8255	Intermediate Similarity	NPC2613
0.8255	Intermediate Similarity	NPC472562
0.8255	Intermediate Similarity	NPC107161
0.8252	Intermediate Similarity	NPC244799
0.8252	Intermediate Similarity	NPC19242
0.8252	Intermediate Similarity	NPC240722
0.8247	Intermediate Similarity	NPC477379
0.8235	Intermediate Similarity	NPC474306
0.8235	Intermediate Similarity	NPC113790
0.8235	Intermediate Similarity	NPC475848
0.8231	Intermediate Similarity	NPC326797
0.8231	Intermediate Similarity	NPC196420
0.8231	Intermediate Similarity	NPC276490
0.8231	Intermediate Similarity	NPC103976
0.8231	Intermediate Similarity	NPC474282
0.8231	Intermediate Similarity	NPC176051
0.8231	Intermediate Similarity	NPC107551
0.8231	Intermediate Similarity	NPC14697
0.8231	Intermediate Similarity	NPC102904
0.8231	Intermediate Similarity	NPC131198
0.8227	Intermediate Similarity	NPC9891
0.8227	Intermediate Similarity	NPC88297
0.8227	Intermediate Similarity	NPC186845
0.8224	Intermediate Similarity	NPC476347
0.8224	Intermediate Similarity	NPC474397
0.8224	Intermediate Similarity	NPC295297
0.8219	Intermediate Similarity	NPC252095
0.8212	Intermediate Similarity	NPC327651
0.8212	Intermediate Similarity	NPC318286

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 NPC475872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	958
0.2-0.3	1901
0.3-0.4	2714
0.4-0.5	1782
0.5-0.6	880
0.6-0.7	495
0.7-0.8	80
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
0.816	Intermediate Similarity	NPD5844	Phase 1
0.7947	Intermediate Similarity	NPD6674	Discontinued
0.7911	Intermediate Similarity	NPD37	Approved
0.7877	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4965	Approved
0.7875	Intermediate Similarity	NPD4966	Approved
0.7871	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD5494	Approved
0.7791	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD6234	Discontinued
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7228	Approved
0.7771	Intermediate Similarity	NPD1653	Approved
0.777	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1613	Approved
0.7755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7549	Discontinued
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7718	Intermediate Similarity	NPD5124	Phase 1
0.7718	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4140	Approved
0.7651	Intermediate Similarity	NPD4481	Phase 3
0.7643	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6100	Approved
0.7632	Intermediate Similarity	NPD6099	Approved
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7240	Approved
0.7576	Intermediate Similarity	NPD7199	Phase 2
0.7568	Intermediate Similarity	NPD3027	Phase 3
0.7518	Intermediate Similarity	NPD7644	Approved
0.7517	Intermediate Similarity	NPD4749	Approved
0.7517	Intermediate Similarity	NPD5327	Phase 3
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD1611	Approved
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5762	Approved
0.7468	Intermediate Similarity	NPD5763	Approved
0.7467	Intermediate Similarity	NPD8032	Phase 2
0.745	Intermediate Similarity	NPD7095	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7436	Intermediate Similarity	NPD4110	Phase 3
0.7436	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2861	Phase 2
0.7417	Intermediate Similarity	NPD4060	Phase 1
0.74	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7985	Registered
0.7396	Intermediate Similarity	NPD7473	Discontinued
0.7391	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3705	Approved
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7378	Intermediate Similarity	NPD3817	Phase 2
0.7372	Intermediate Similarity	NPD1652	Phase 2
0.7368	Intermediate Similarity	NPD3657	Discovery
0.7362	Intermediate Similarity	NPD1934	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7819	Suspended
0.7317	Intermediate Similarity	NPD1465	Phase 2
0.7315	Intermediate Similarity	NPD3018	Phase 2
0.7314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3620	Phase 2
0.7303	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5691	Approved
0.7286	Intermediate Similarity	NPD5535	Approved
0.7261	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5735	Approved
0.725	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6166	Phase 2
0.723	Intermediate Similarity	NPD6696	Suspended
0.723	Intermediate Similarity	NPD8651	Approved
0.7226	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7215	Intermediate Similarity	NPD7466	Approved
0.7212	Intermediate Similarity	NPD2801	Approved
0.7212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2981	Phase 2
0.72	Intermediate Similarity	NPD2237	Approved
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3496	Discontinued
0.7188	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5585	Approved
0.7168	Intermediate Similarity	NPD7074	Phase 3
0.7162	Intermediate Similarity	NPD2983	Phase 2
0.7162	Intermediate Similarity	NPD2982	Phase 2
0.7161	Intermediate Similarity	NPD6111	Discontinued
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7906	Approved
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7124	Phase 2
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7118	Intermediate Similarity	NPD3051	Approved
0.7118	Intermediate Similarity	NPD3787	Discontinued
0.7115	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7054	Approved
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7101	Intermediate Similarity	NPD5677	Discontinued
0.7099	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD6353	Approved
0.7083	Intermediate Similarity	NPD7075	Discontinued
0.7079	Intermediate Similarity	NPD4663	Approved
0.7073	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2438	Suspended
0.7069	Intermediate Similarity	NPD7472	Approved
0.7066	Intermediate Similarity	NPD5402	Approved
0.7066	Intermediate Similarity	NPD5353	Approved
0.7066	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD6959	Discontinued
0.7041	Intermediate Similarity	NPD919	Approved
0.7025	Intermediate Similarity	NPD7266	Discontinued
0.7024	Intermediate Similarity	NPD7768	Phase 2
0.7014	Intermediate Similarity	NPD6671	Approved
0.7014	Intermediate Similarity	NPD7157	Approved
0.7011	Intermediate Similarity	NPD8156	Discontinued
0.7007	Intermediate Similarity	NPD4626	Approved
0.7007	Intermediate Similarity	NPD1778	Approved
0.7006	Intermediate Similarity	NPD7312	Approved
0.7006	Intermediate Similarity	NPD7311	Approved
0.7006	Intermediate Similarity	NPD4577	Approved
0.7006	Intermediate Similarity	NPD7310	Approved
0.7006	Intermediate Similarity	NPD7313	Approved
0.7006	Intermediate Similarity	NPD4578	Approved
0.7	Intermediate Similarity	NPD8166	Discontinued
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD3750	Approved
0.6988	Remote Similarity	NPD7411	Suspended
0.6986	Remote Similarity	NPD1548	Phase 1
0.6982	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2969	Approved
0.6977	Remote Similarity	NPD2970	Approved
0.6973	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2979	Phase 3
0.6966	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7309	Approved
0.6962	Remote Similarity	NPD2796	Approved
0.6954	Remote Similarity	NPD8099	Discontinued
0.6954	Remote Similarity	NPD8251	Approved
0.6954	Remote Similarity	NPD8252	Approved
0.6949	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD4359	Approved
0.6928	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2968	Approved
0.691	Remote Similarity	NPD2971	Approved
0.6909	Remote Similarity	NPD3687	Approved
0.6909	Remote Similarity	NPD3686	Approved
0.6893	Remote Similarity	NPD7251	Discontinued
0.6892	Remote Similarity	NPD17	Approved
0.689	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2676	Approved
0.689	Remote Similarity	NPD2675	Approved
0.6875	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6799	Approved
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD2974	Approved
0.6865	Remote Similarity	NPD2975	Approved
0.6865	Remote Similarity	NPD2973	Approved
0.6865	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5736	Approved
0.686	Remote Similarity	NPD1247	Approved
0.6857	Remote Similarity	NPD3751	Discontinued
0.6857	Remote Similarity	NPD3818	Discontinued
0.6855	Remote Similarity	NPD3539	Phase 1
0.6849	Remote Similarity	NPD7340	Approved
0.6845	Remote Similarity	NPD4580	Approved
0.6845	Remote Similarity	NPD6801	Discontinued
0.6842	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD3266	Approved
0.6842	Remote Similarity	NPD3267	Approved
0.6839	Remote Similarity	NPD2489	Approved
0.6839	Remote Similarity	NPD1296	Phase 2
0.6839	Remote Similarity	NPD27	Approved
0.6836	Remote Similarity	NPD6797	Phase 2
0.6831	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7447	Phase 1
0.6829	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD2534	Approved
0.6829	Remote Similarity	NPD2532	Approved
0.6826	Remote Similarity	NPD4380	Phase 2
0.6826	Remote Similarity	NPD7028	Phase 2
0.6825	Remote Similarity	NPD7680	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