NPASS Compound

Structure

NPC142654 OpenBabel07101718322D 27 30 0 0 1 0 0 0 0 0999 V2000 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 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 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1713 3.0497 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 2.5981 -2.5000 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 -2.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.3955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 2.0316 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 0.8660 -1.5000 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 -3.9346 0.6226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1211 -1.2045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 1.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1767 2.9451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 5 27 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 16 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 1 0 0 0 17 22 1 1 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 22 3 1 1 0 0 0 23 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.23
Volume:	396.753
LogP:	4.72
LogD:	3.495
LogS:	-4.211
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.061
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.82
MDCK Permeability:	1.9189383237971924e-05
Pgp-inhibitor:	0.915
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.826
30% Bioavailability (F30%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.076
Plasma Protein Binding (PPB):	98.75316619873047%
Volume Distribution (VD):	1.342
Pgp-substrate:	3.1060521602630615%

ADMET: Metabolism

CYP1A2-inhibitor:	0.202
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.706
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.434
CYP2D6-substrate:	0.639
CYP3A4-inhibitor:	0.222
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	11.983
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.812
Skin Sensitization:	0.914
Carcinogencity:	0.145
Eye Corrosion:	0.01
Eye Irritation:	0.827
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC142654

Natural Product ID:	NPC142654
*Common Name:**	Pelorol
IUPAC Name:	methyl (4aS,6aR,11aR,11bS)-9,10-dihydroxy-4,4,6a,11b-tetramethyl-1,2,3,4a,5,6,11,11a-octahydrobenzo[a]fluorene-7-carboxylate
Synonyms:	Pelorol
Standard InCHIKey:	FFBLMLRQAKGTJN-VQDLLJBESA-N
Standard InCHI:	InChI=1S/C23H32O4/c1-21(2)8-6-9-22(3)16(21)7-10-23(4)17(22)12-13-18(23)14(20(26)27-5)11-15(24)19(13)25/h11,16-17,24-25H,6-10,12H2,1-5H3/t16-,17+,22-,23+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2Cc2c1c(cc(c2O)O)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487183
PubChem CID:	10067895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978215]
NPO33485	petrosaspongia metachromia	Species	Thorectidae	Eukaryota	n.a.	Micronesian	n.a.	PMID[10978216]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542344]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21155589]
NPO25355	Dactylospongia elegans	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964793]
NPO25355	Dactylospongia elegans	Species	Thorectidae	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	3
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	17.4	ug.mL-1	PMID[493450]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.786	ug.mL-1	PMID[493450]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.911	ug.mL-1	PMID[493450]
NPT140	Organism	Artemia	Artemia	LC50	=	5.0	ug.mL-1	PMID[493451]

☑ 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 NPC142654 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	350
0.1-0.2	1414
0.2-0.3	2815
0.3-0.4	5896
0.4-0.5	10621
0.5-0.6	7054
0.6-0.7	9146
0.7-0.8	5229
0.8-0.85	131
0.85-0.9	35
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.958	High Similarity	NPC75295
0.9444	High Similarity	NPC258856
0.9195	High Similarity	NPC124842
0.9073	High Similarity	NPC62051
0.8859	High Similarity	NPC191899
0.8859	High Similarity	NPC246229
0.8844	High Similarity	NPC184935
0.88	High Similarity	NPC470757
0.8742	High Similarity	NPC200726
0.8741	High Similarity	NPC239855
0.8733	High Similarity	NPC58752
0.8733	High Similarity	NPC474991
0.8707	High Similarity	NPC470035
0.8707	High Similarity	NPC327187
0.8707	High Similarity	NPC471853
0.869	High Similarity	NPC326847
0.8688	High Similarity	NPC177362
0.8681	High Similarity	NPC477594
0.8681	High Similarity	NPC293454
0.8667	High Similarity	NPC470038
0.8667	High Similarity	NPC84786
0.8634	High Similarity	NPC202428
0.8634	High Similarity	NPC266545
0.863	High Similarity	NPC477592
0.8621	High Similarity	NPC477596
0.86	High Similarity	NPC126707
0.8571	High Similarity	NPC221249
0.8571	High Similarity	NPC477593
0.8562	High Similarity	NPC303989
0.8562	High Similarity	NPC475111
0.8553	High Similarity	NPC127046
0.8523	High Similarity	NPC477595
0.8503	High Similarity	NPC49911
0.8503	High Similarity	NPC277559
0.8497	Intermediate Similarity	NPC279442
0.8497	Intermediate Similarity	NPC474306
0.8497	Intermediate Similarity	NPC475848
0.8491	Intermediate Similarity	NPC266365
0.8483	Intermediate Similarity	NPC111845
0.8477	Intermediate Similarity	NPC309169
0.8477	Intermediate Similarity	NPC196941
0.8467	Intermediate Similarity	NPC248068
0.8446	Intermediate Similarity	NPC230811
0.8442	Intermediate Similarity	NPC474305
0.8431	Intermediate Similarity	NPC52692
0.8431	Intermediate Similarity	NPC10842
0.8428	Intermediate Similarity	NPC185617
0.8421	Intermediate Similarity	NPC8102
0.8421	Intermediate Similarity	NPC66894
0.8418	Intermediate Similarity	NPC167098
0.8418	Intermediate Similarity	NPC296044
0.8408	Intermediate Similarity	NPC472835
0.84	Intermediate Similarity	NPC2681
0.84	Intermediate Similarity	NPC272907
0.8387	Intermediate Similarity	NPC470037
0.8385	Intermediate Similarity	NPC161151
0.8356	Intermediate Similarity	NPC138472
0.8356	Intermediate Similarity	NPC4170
0.8356	Intermediate Similarity	NPC476282
0.8354	Intermediate Similarity	NPC471968
0.8333	Intermediate Similarity	NPC476534
0.8333	Intermediate Similarity	NPC3218
0.8322	Intermediate Similarity	NPC112135
0.8313	Intermediate Similarity	NPC21046
0.8312	Intermediate Similarity	NPC5568
0.8311	Intermediate Similarity	NPC156307
0.8302	Intermediate Similarity	NPC143328
0.8301	Intermediate Similarity	NPC225351
0.8299	Intermediate Similarity	NPC204582
0.8289	Intermediate Similarity	NPC50954
0.8272	Intermediate Similarity	NPC100420
0.8264	Intermediate Similarity	NPC229894
0.8261	Intermediate Similarity	NPC131905
0.8258	Intermediate Similarity	NPC471852
0.8255	Intermediate Similarity	NPC471152
0.8243	Intermediate Similarity	NPC153088
0.8239	Intermediate Similarity	NPC109765
0.8239	Intermediate Similarity	NPC213401
0.8235	Intermediate Similarity	NPC260152
0.8228	Intermediate Similarity	NPC281703
0.8228	Intermediate Similarity	NPC125487
0.8224	Intermediate Similarity	NPC176030
0.8224	Intermediate Similarity	NPC314271
0.8224	Intermediate Similarity	NPC192597
0.8224	Intermediate Similarity	NPC169214
0.8224	Intermediate Similarity	NPC229218
0.8224	Intermediate Similarity	NPC141817
0.8219	Intermediate Similarity	NPC18798
0.8219	Intermediate Similarity	NPC243305
0.8217	Intermediate Similarity	NPC302783
0.8217	Intermediate Similarity	NPC92747
0.8217	Intermediate Similarity	NPC473201
0.8217	Intermediate Similarity	NPC265862
0.8212	Intermediate Similarity	NPC290664
0.8212	Intermediate Similarity	NPC168471
0.821	Intermediate Similarity	NPC144843
0.8207	Intermediate Similarity	NPC117899
0.8205	Intermediate Similarity	NPC327962
0.8194	Intermediate Similarity	NPC158654
0.8187	Intermediate Similarity	NPC202495
0.8176	Intermediate Similarity	NPC202225
0.8176	Intermediate Similarity	NPC213122
0.817	Intermediate Similarity	NPC469615
0.8165	Intermediate Similarity	NPC205392
0.8165	Intermediate Similarity	NPC105942
0.8165	Intermediate Similarity	NPC161159
0.8158	Intermediate Similarity	NPC91546
0.8153	Intermediate Similarity	NPC225854
0.8153	Intermediate Similarity	NPC280295
0.8151	Intermediate Similarity	NPC108129
0.8148	Intermediate Similarity	NPC469889
0.8146	Intermediate Similarity	NPC471819
0.8138	Intermediate Similarity	NPC193203
0.8137	Intermediate Similarity	NPC239118
0.8137	Intermediate Similarity	NPC45846
0.8133	Intermediate Similarity	NPC472803
0.8133	Intermediate Similarity	NPC119542
0.8129	Intermediate Similarity	NPC268366
0.8125	Intermediate Similarity	NPC25850
0.8125	Intermediate Similarity	NPC276815
0.8117	Intermediate Similarity	NPC275278
0.8117	Intermediate Similarity	NPC469683
0.8117	Intermediate Similarity	NPC471305
0.8113	Intermediate Similarity	NPC107109
0.811	Intermediate Similarity	NPC211592
0.8108	Intermediate Similarity	NPC49742
0.8105	Intermediate Similarity	NPC477873
0.8105	Intermediate Similarity	NPC469447
0.8101	Intermediate Similarity	NPC267091
0.8101	Intermediate Similarity	NPC78505
0.8101	Intermediate Similarity	NPC75377
0.8095	Intermediate Similarity	NPC471851
0.8095	Intermediate Similarity	NPC291001
0.8092	Intermediate Similarity	NPC469911
0.8092	Intermediate Similarity	NPC473612
0.8092	Intermediate Similarity	NPC475907
0.8089	Intermediate Similarity	NPC162569
0.8089	Intermediate Similarity	NPC35160
0.8089	Intermediate Similarity	NPC179128
0.8089	Intermediate Similarity	NPC267469
0.8089	Intermediate Similarity	NPC247219
0.8089	Intermediate Similarity	NPC87630
0.8089	Intermediate Similarity	NPC116292
0.8089	Intermediate Similarity	NPC261322
0.8089	Intermediate Similarity	NPC9099
0.8086	Intermediate Similarity	NPC47623
0.8082	Intermediate Similarity	NPC30174
0.8082	Intermediate Similarity	NPC94810
0.8082	Intermediate Similarity	NPC226855
0.8079	Intermediate Similarity	NPC61398
0.8079	Intermediate Similarity	NPC469680
0.8079	Intermediate Similarity	NPC416
0.8079	Intermediate Similarity	NPC471974
0.8079	Intermediate Similarity	NPC469681
0.8077	Intermediate Similarity	NPC155910
0.8077	Intermediate Similarity	NPC17042
0.8077	Intermediate Similarity	NPC119767
0.8077	Intermediate Similarity	NPC81835
0.8077	Intermediate Similarity	NPC477483
0.8077	Intermediate Similarity	NPC325032
0.8075	Intermediate Similarity	NPC283301
0.8075	Intermediate Similarity	NPC37543
0.8075	Intermediate Similarity	NPC199463
0.8075	Intermediate Similarity	NPC158542
0.8069	Intermediate Similarity	NPC176130
0.8069	Intermediate Similarity	NPC84672
0.8069	Intermediate Similarity	NPC78364
0.8069	Intermediate Similarity	NPC69424
0.8067	Intermediate Similarity	NPC156892
0.8067	Intermediate Similarity	NPC7464
0.8065	Intermediate Similarity	NPC208293
0.8063	Intermediate Similarity	NPC471456
0.8063	Intermediate Similarity	NPC472807
0.8061	Intermediate Similarity	NPC165460
0.8061	Intermediate Similarity	NPC263212
0.8054	Intermediate Similarity	NPC477893
0.8054	Intermediate Similarity	NPC477896
0.8052	Intermediate Similarity	NPC477207
0.8052	Intermediate Similarity	NPC199936
0.8052	Intermediate Similarity	NPC100242
0.805	Intermediate Similarity	NPC180944
0.805	Intermediate Similarity	NPC131121
0.8049	Intermediate Similarity	NPC319200
0.8049	Intermediate Similarity	NPC45943
0.8049	Intermediate Similarity	NPC187491
0.8047	Intermediate Similarity	NPC475054
0.8039	Intermediate Similarity	NPC35212
0.8038	Intermediate Similarity	NPC243891
0.8038	Intermediate Similarity	NPC205766
0.8038	Intermediate Similarity	NPC31132
0.8026	Intermediate Similarity	NPC191280
0.8025	Intermediate Similarity	NPC472299
0.8025	Intermediate Similarity	NPC218818
0.8025	Intermediate Similarity	NPC471750
0.8025	Intermediate Similarity	NPC470339
0.8025	Intermediate Similarity	NPC4950
0.8013	Intermediate Similarity	NPC194579
0.8013	Intermediate Similarity	NPC147418
0.8013	Intermediate Similarity	NPC147250
0.8013	Intermediate Similarity	NPC476535

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 NPC142654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	892
0.2-0.3	1616
0.3-0.4	2651
0.4-0.5	2078
0.5-0.6	1091
0.6-0.7	442
0.7-0.8	69
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
0.8061	Intermediate Similarity	NPD7473	Discontinued
0.8039	Intermediate Similarity	NPD8166	Discontinued
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7867	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3764	Approved
0.7711	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD7003	Approved
0.7669	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD5844	Phase 1
0.7644	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7458	Discontinued
0.7616	Intermediate Similarity	NPD6663	Approved
0.7614	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2533	Approved
0.761	Intermediate Similarity	NPD2532	Approved
0.761	Intermediate Similarity	NPD2534	Approved
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD5736	Approved
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD6273	Approved
0.7561	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6190	Approved
0.7531	Intermediate Similarity	NPD3226	Approved
0.7517	Intermediate Similarity	NPD3019	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7819	Suspended
0.7452	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD2935	Discontinued
0.7436	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7401	Intermediate Similarity	NPD8150	Discontinued
0.7397	Intermediate Similarity	NPD2932	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD7228	Approved
0.7375	Intermediate Similarity	NPD7236	Approved
0.7365	Intermediate Similarity	NPD4966	Approved
0.7365	Intermediate Similarity	NPD4965	Approved
0.7365	Intermediate Similarity	NPD9269	Phase 2
0.7365	Intermediate Similarity	NPD4967	Phase 2
0.7358	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2801	Approved
0.7338	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD943	Approved
0.7338	Intermediate Similarity	NPD3620	Phase 2
0.7333	Intermediate Similarity	NPD1470	Approved
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1934	Approved
0.7284	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD8032	Phase 2
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9545	Approved
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.7222	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD7075	Discontinued
0.7195	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6959	Discontinued
0.7184	Intermediate Similarity	NPD3818	Discontinued
0.7181	Intermediate Similarity	NPD1201	Approved
0.7169	Intermediate Similarity	NPD7028	Phase 2
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD7239	Suspended
0.7152	Intermediate Similarity	NPD1283	Approved
0.7143	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5494	Approved
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7124	Intermediate Similarity	NPD9494	Approved
0.7114	Intermediate Similarity	NPD3023	Approved
0.7114	Intermediate Similarity	NPD3026	Approved
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7108	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6100	Approved
0.7107	Intermediate Similarity	NPD6099	Approved
0.7105	Intermediate Similarity	NPD3094	Phase 2
0.7101	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD3024	Approved
0.7095	Intermediate Similarity	NPD3025	Approved
0.7095	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9268	Approved
0.7081	Intermediate Similarity	NPD2800	Approved
0.7073	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6166	Phase 2
0.7069	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3092	Approved
0.7066	Intermediate Similarity	NPD6599	Discontinued
0.7066	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD7768	Phase 2
0.7052	Intermediate Similarity	NPD5710	Approved
0.7052	Intermediate Similarity	NPD5711	Approved
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD4626	Approved
0.7039	Intermediate Similarity	NPD1876	Approved
0.7037	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4110	Phase 3
0.7025	Intermediate Similarity	NPD6651	Approved
0.7024	Intermediate Similarity	NPD7411	Suspended
0.7018	Intermediate Similarity	NPD3749	Approved
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD4140	Approved
0.7006	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7177	Discontinued
0.6986	Remote Similarity	NPD5951	Approved
0.6982	Remote Similarity	NPD6801	Discontinued
0.6962	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD1281	Approved
0.6951	Remote Similarity	NPD3300	Phase 2
0.6949	Remote Similarity	NPD7054	Approved
0.6947	Remote Similarity	NPD7497	Discontinued
0.6937	Remote Similarity	NPD1510	Phase 2
0.6933	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD6385	Approved
0.6923	Remote Similarity	NPD6873	Phase 2
0.6923	Remote Similarity	NPD7008	Discontinued
0.6918	Remote Similarity	NPD1607	Approved
0.6913	Remote Similarity	NPD3091	Approved
0.691	Remote Similarity	NPD7472	Approved
0.6908	Remote Similarity	NPD1608	Approved
0.6908	Remote Similarity	NPD3972	Approved
0.6906	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3455	Phase 2
0.6901	Remote Similarity	NPD5977	Approved
0.6901	Remote Similarity	NPD5978	Approved
0.6899	Remote Similarity	NPD2979	Phase 3
0.6899	Remote Similarity	NPD1240	Approved
0.6893	Remote Similarity	NPD7799	Discontinued
0.6889	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2313	Discontinued
0.6875	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5735	Approved
0.6855	Remote Similarity	NPD447	Suspended
0.6852	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4624	Approved
0.6839	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6559	Discontinued
0.6833	Remote Similarity	NPD6764	Approved
0.6833	Remote Similarity	NPD6765	Approved
0.6833	Remote Similarity	NPD7251	Discontinued
0.6832	Remote Similarity	NPD3748	Approved
0.6823	Remote Similarity	NPD8319	Approved
0.6823	Remote Similarity	NPD8320	Phase 1
0.6821	Remote Similarity	NPD4059	Approved
0.6818	Remote Similarity	NPD6696	Suspended
0.6815	Remote Similarity	NPD7095	Approved
0.6807	Remote Similarity	NPD6799	Approved
0.6779	Remote Similarity	NPD9493	Approved
0.6778	Remote Similarity	NPD6797	Phase 2
0.6774	Remote Similarity	NPD1164	Approved
0.6772	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7435	Discontinued
0.6769	Remote Similarity	NPD8151	Discontinued
0.6768	Remote Similarity	NPD6674	Discontinued
0.6763	Remote Similarity	NPD7057	Phase 3
0.6763	Remote Similarity	NPD7058	Phase 2
0.6759	Remote Similarity	NPD3022	Approved
0.6759	Remote Similarity	NPD3021	Approved
0.6755	Remote Similarity	NPD5691	Approved
0.6748	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6002	Phase 3
0.6748	Remote Similarity	NPD2344	Approved
0.6748	Remote Similarity	NPD6004	Phase 3
0.6748	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6005	Phase 3
0.6736	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2798	Approved
0.673	Remote Similarity	NPD7961	Discontinued
0.6724	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3095	Discontinued
0.6711	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD17	Approved
0.6707	Remote Similarity	NPD1549	Phase 2
0.6705	Remote Similarity	NPD5353	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