NPASS Compound

Structure

NPC224884 OpenBabel07101718332D 29 31 0 0 1 0 0 0 0 0999 V2000 2.7096 -4.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0810 2.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5514 -0.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0720 4.3510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7096 -3.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8619 -2.9903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8619 -2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0142 -1.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2243 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0720 1.4145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3766 2.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5289 -0.0538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3766 1.4145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5289 0.9250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6812 -0.5432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0720 2.3933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0142 -0.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2243 2.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1665 -0.0538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1665 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6812 1.4145 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9197 2.8827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8619 -0.0538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8619 1.9039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8819 1.2959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 0.0731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2243 3.8616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 4 29 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 22 1 1 0 0 0 15 19 1 0 0 0 0 15 23 1 1 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 27 2 0 0 0 0 22 2 1 1 0 0 0 23 3 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.17
Volume:	412.344
LogP:	2.45
LogD:	1.863
LogS:	-4.012
# Rotatable Bonds:	5
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.251
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.605
MDCK Permeability:	2.3223425159812905e-05
Pgp-inhibitor:	0.238
Pgp-substrate:	0.262
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.921
Plasma Protein Binding (PPB):	93.8561019897461%
Volume Distribution (VD):	0.518
Pgp-substrate:	3.5981807708740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.545
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.84

ADMET: Excretion

Clearance (CL):	11.034
Half-life (T1/2):	0.413

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.403
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.852
Carcinogencity:	0.891
Eye Corrosion:	0.256
Eye Irritation:	0.339
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC224884

Natural Product ID:	NPC224884
*Common Name:**	Sorbicatechol B
IUPAC Name:	(1S,2S,4R,6Z,8S)-2-hydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dienylidene]-8-(4-hydroxy-3-methoxyphenyl)-2,4-dimethylbicyclo[2.2.2]octane-3,5-dione
Synonyms:
Standard InCHIKey:	GSRGQKYQEBYBAG-NAUUYRRVSA-N
Standard InCHI:	InChI=1S/C23H26O6/c1-5-6-7-8-17(25)19-15-12-14(13-9-10-16(24)18(11-13)29-4)22(2,20(19)26)21(27)23(15,3)28/h5-11,14-15,24-25,28H,12H2,1-4H3/b6-5+,8-7+,19-17-/t14-,15-,22+,23-/m0/s1
SMILES:	C/C=C/C=C/C(=C/1[C@@H]2C[C@H]([C@](C1=O)(C(=O)[C@@]2(C)O)C)c1ccc(c(c1)OC)O)/O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109424
PubChem CID:	76328404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002099] Cyclohexylphenols

*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
NPO33259	penicillium chrysogenum pjx-17	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24495078]

☑ 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
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	113000.0	nM	PMID[478358]

☑ 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 NPC224884 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	397
0.1-0.2	1504
0.2-0.3	2987
0.3-0.4	7238
0.4-0.5	10528
0.5-0.6	6158
0.6-0.7	10871
0.7-0.8	2911
0.8-0.85	78
0.85-0.9	23
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC209085
0.8912	High Similarity	NPC237441
0.8904	High Similarity	NPC52692
0.8857	High Similarity	NPC252343
0.8819	High Similarity	NPC229218
0.8819	High Similarity	NPC192597
0.8819	High Similarity	NPC141817
0.8819	High Similarity	NPC169214
0.8819	High Similarity	NPC176030
0.88	High Similarity	NPC305710
0.8777	High Similarity	NPC239302
0.875	High Similarity	NPC472410
0.8714	High Similarity	NPC327410
0.8699	High Similarity	NPC196941
0.8699	High Similarity	NPC309169
0.8696	High Similarity	NPC304622
0.8681	High Similarity	NPC78987
0.8681	High Similarity	NPC82336
0.8671	High Similarity	NPC132723
0.8671	High Similarity	NPC76032
0.8633	High Similarity	NPC172673
0.8613	High Similarity	NPC92207
0.8613	High Similarity	NPC84076
0.8613	High Similarity	NPC303680
0.8613	High Similarity	NPC90128
0.8613	High Similarity	NPC127937
0.86	High Similarity	NPC475454
0.86	High Similarity	NPC473680
0.86	High Similarity	NPC475311
0.86	High Similarity	NPC473579
0.8552	High Similarity	NPC29599
0.8551	High Similarity	NPC123722
0.8551	High Similarity	NPC5018
0.8551	High Similarity	NPC151167
0.8551	High Similarity	NPC123228
0.8551	High Similarity	NPC276466
0.854	High Similarity	NPC53305
0.854	High Similarity	NPC257589
0.8529	High Similarity	NPC163083
0.8478	Intermediate Similarity	NPC179777
0.8478	Intermediate Similarity	NPC276014
0.8477	Intermediate Similarity	NPC118033
0.8477	Intermediate Similarity	NPC475718
0.8421	Intermediate Similarity	NPC472838
0.8421	Intermediate Similarity	NPC475579
0.8421	Intermediate Similarity	NPC124842
0.8421	Intermediate Similarity	NPC473773
0.8421	Intermediate Similarity	NPC306011
0.8406	Intermediate Similarity	NPC228771
0.8406	Intermediate Similarity	NPC266705
0.8406	Intermediate Similarity	NPC29008
0.8394	Intermediate Similarity	NPC257976
0.8394	Intermediate Similarity	NPC242372
0.8394	Intermediate Similarity	NPC4181
0.8394	Intermediate Similarity	NPC164778
0.8389	Intermediate Similarity	NPC160777
0.8389	Intermediate Similarity	NPC73416
0.8382	Intermediate Similarity	NPC201777
0.8366	Intermediate Similarity	NPC105942
0.8366	Intermediate Similarity	NPC205392
0.8357	Intermediate Similarity	NPC226661
0.8356	Intermediate Similarity	NPC322021
0.8355	Intermediate Similarity	NPC295977
0.8355	Intermediate Similarity	NPC58310
0.8345	Intermediate Similarity	NPC471152
0.8344	Intermediate Similarity	NPC474556
0.8333	Intermediate Similarity	NPC95485
0.8333	Intermediate Similarity	NPC152209
0.8333	Intermediate Similarity	NPC273686
0.8333	Intermediate Similarity	NPC39361
0.8333	Intermediate Similarity	NPC89504
0.8333	Intermediate Similarity	NPC58752
0.8333	Intermediate Similarity	NPC312404
0.8333	Intermediate Similarity	NPC88065
0.8322	Intermediate Similarity	NPC91694
0.8322	Intermediate Similarity	NPC300603
0.8321	Intermediate Similarity	NPC114298
0.8312	Intermediate Similarity	NPC62051
0.8309	Intermediate Similarity	NPC158949
0.8288	Intermediate Similarity	NPC469680
0.8288	Intermediate Similarity	NPC471974
0.8288	Intermediate Similarity	NPC469681
0.8278	Intermediate Similarity	NPC470757
0.8278	Intermediate Similarity	NPC58373
0.8276	Intermediate Similarity	NPC90431
0.8273	Intermediate Similarity	NPC9067
0.8267	Intermediate Similarity	NPC225351
0.8264	Intermediate Similarity	NPC300776
0.8264	Intermediate Similarity	NPC68779
0.8264	Intermediate Similarity	NPC176814
0.8264	Intermediate Similarity	NPC4982
0.8264	Intermediate Similarity	NPC5310
0.8261	Intermediate Similarity	NPC160900
0.8261	Intermediate Similarity	NPC18984
0.8261	Intermediate Similarity	NPC229084
0.8261	Intermediate Similarity	NPC106659
0.8247	Intermediate Similarity	NPC164912
0.8243	Intermediate Similarity	NPC253722
0.8243	Intermediate Similarity	NPC31751
0.8243	Intermediate Similarity	NPC253481
0.8239	Intermediate Similarity	NPC65935
0.8239	Intermediate Similarity	NPC244246
0.8239	Intermediate Similarity	NPC311419
0.8239	Intermediate Similarity	NPC215941
0.8239	Intermediate Similarity	NPC123196
0.8239	Intermediate Similarity	NPC137427
0.8239	Intermediate Similarity	NPC319282
0.8239	Intermediate Similarity	NPC275724
0.8231	Intermediate Similarity	NPC294330
0.8227	Intermediate Similarity	NPC201069
0.8227	Intermediate Similarity	NPC307050
0.8227	Intermediate Similarity	NPC277458
0.8224	Intermediate Similarity	NPC132810
0.8224	Intermediate Similarity	NPC264229
0.8224	Intermediate Similarity	NPC46549
0.8212	Intermediate Similarity	NPC471970
0.8212	Intermediate Similarity	NPC30720
0.8207	Intermediate Similarity	NPC113295
0.82	Intermediate Similarity	NPC8493
0.82	Intermediate Similarity	NPC307205
0.82	Intermediate Similarity	NPC469375
0.82	Intermediate Similarity	NPC145301
0.82	Intermediate Similarity	NPC294679
0.82	Intermediate Similarity	NPC144247
0.8188	Intermediate Similarity	NPC11314
0.8188	Intermediate Similarity	NPC286573
0.8182	Intermediate Similarity	NPC473201
0.8182	Intermediate Similarity	NPC118427
0.8182	Intermediate Similarity	NPC78505
0.8182	Intermediate Similarity	NPC144283
0.8182	Intermediate Similarity	NPC302783
0.817	Intermediate Similarity	NPC261322
0.8163	Intermediate Similarity	NPC245760
0.8163	Intermediate Similarity	NPC23667
0.8163	Intermediate Similarity	NPC46242
0.8163	Intermediate Similarity	NPC28592
0.8163	Intermediate Similarity	NPC91887
0.8163	Intermediate Similarity	NPC114333
0.8163	Intermediate Similarity	NPC284409
0.8163	Intermediate Similarity	NPC297797
0.8163	Intermediate Similarity	NPC51531
0.8163	Intermediate Similarity	NPC473779
0.8163	Intermediate Similarity	NPC165191
0.8163	Intermediate Similarity	NPC157284
0.8163	Intermediate Similarity	NPC5014
0.8163	Intermediate Similarity	NPC50615
0.8163	Intermediate Similarity	NPC477849
0.8163	Intermediate Similarity	NPC149773
0.8163	Intermediate Similarity	NPC289358
0.8163	Intermediate Similarity	NPC42384
0.8163	Intermediate Similarity	NPC469857
0.8163	Intermediate Similarity	NPC473479
0.8162	Intermediate Similarity	NPC299406
0.8158	Intermediate Similarity	NPC77598
0.8156	Intermediate Similarity	NPC20404
0.8156	Intermediate Similarity	NPC293641
0.8156	Intermediate Similarity	NPC12022
0.8156	Intermediate Similarity	NPC20287
0.8143	Intermediate Similarity	NPC3221
0.8138	Intermediate Similarity	NPC311256
0.8133	Intermediate Similarity	NPC16353
0.8133	Intermediate Similarity	NPC50954
0.8133	Intermediate Similarity	NPC46161
0.8133	Intermediate Similarity	NPC239608
0.8133	Intermediate Similarity	NPC46880
0.8121	Intermediate Similarity	NPC84273
0.8112	Intermediate Similarity	NPC66905
0.8108	Intermediate Similarity	NPC474784
0.8105	Intermediate Similarity	NPC292206
0.8102	Intermediate Similarity	NPC117780
0.8102	Intermediate Similarity	NPC232316
0.8102	Intermediate Similarity	NPC56214
0.8102	Intermediate Similarity	NPC165133
0.8102	Intermediate Similarity	NPC227217
0.8102	Intermediate Similarity	NPC95614
0.8102	Intermediate Similarity	NPC242885
0.8099	Intermediate Similarity	NPC278308
0.8092	Intermediate Similarity	NPC273798
0.8089	Intermediate Similarity	NPC213401
0.8089	Intermediate Similarity	NPC279605
0.8089	Intermediate Similarity	NPC288353
0.8079	Intermediate Similarity	NPC19862
0.8079	Intermediate Similarity	NPC258671
0.8079	Intermediate Similarity	NPC53884
0.8079	Intermediate Similarity	NPC271607
0.8079	Intermediate Similarity	NPC280717
0.8079	Intermediate Similarity	NPC469856
0.8079	Intermediate Similarity	NPC469854
0.8079	Intermediate Similarity	NPC235195
0.8077	Intermediate Similarity	NPC127172
0.8071	Intermediate Similarity	NPC15127
0.8067	Intermediate Similarity	NPC471971
0.8067	Intermediate Similarity	NPC30846
0.8067	Intermediate Similarity	NPC471972
0.8067	Intermediate Similarity	NPC477873
0.8067	Intermediate Similarity	NPC469855
0.8067	Intermediate Similarity	NPC469447
0.8065	Intermediate Similarity	NPC70320
0.8058	Intermediate Similarity	NPC30462
0.8054	Intermediate Similarity	NPC19158

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 NPC224884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	895
0.2-0.3	1538
0.3-0.4	2653
0.4-0.5	2111
0.5-0.6	1066
0.6-0.7	481
0.7-0.8	51
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD8166	Discontinued
0.8	Intermediate Similarity	NPD3620	Phase 2
0.8	Intermediate Similarity	NPD7028	Phase 2
0.8	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD7095	Approved
0.7754	Intermediate Similarity	NPD5536	Phase 2
0.7714	Intermediate Similarity	NPD3019	Approved
0.7706	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD9494	Approved
0.7654	Intermediate Similarity	NPD6234	Discontinued
0.7647	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4110	Phase 3
0.7635	Intermediate Similarity	NPD4060	Phase 1
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.759	Intermediate Similarity	NPD7473	Discontinued
0.7589	Intermediate Similarity	NPD2932	Approved
0.7574	Intermediate Similarity	NPD228	Approved
0.7562	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD8127	Discontinued
0.7532	Intermediate Similarity	NPD7003	Approved
0.7531	Intermediate Similarity	NPD3882	Suspended
0.7518	Intermediate Similarity	NPD1651	Approved
0.7516	Intermediate Similarity	NPD2801	Approved
0.7515	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7484	Intermediate Similarity	NPD7458	Discontinued
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7453	Intermediate Similarity	NPD1934	Approved
0.745	Intermediate Similarity	NPD8032	Phase 2
0.7448	Intermediate Similarity	NPD1283	Approved
0.7431	Intermediate Similarity	NPD3972	Approved
0.7425	Intermediate Similarity	NPD6166	Phase 2
0.7425	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4965	Approved
0.7423	Intermediate Similarity	NPD4966	Approved
0.7423	Intermediate Similarity	NPD4967	Phase 2
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6099	Approved
0.7386	Intermediate Similarity	NPD6100	Approved
0.7383	Intermediate Similarity	NPD3268	Approved
0.7372	Intermediate Similarity	NPD6190	Approved
0.7347	Intermediate Similarity	NPD4624	Approved
0.7343	Intermediate Similarity	NPD4626	Approved
0.7337	Intermediate Similarity	NPD7228	Approved
0.7315	Intermediate Similarity	NPD3027	Phase 3
0.7308	Intermediate Similarity	NPD4628	Phase 3
0.7308	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3021	Approved
0.7299	Intermediate Similarity	NPD3022	Approved
0.7296	Intermediate Similarity	NPD1512	Approved
0.7296	Intermediate Similarity	NPD6273	Approved
0.7292	Intermediate Similarity	NPD3023	Approved
0.7292	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD3025	Approved
0.726	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1281	Approved
0.7237	Intermediate Similarity	NPD3657	Discovery
0.7233	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2488	Approved
0.7232	Intermediate Similarity	NPD2490	Approved
0.7219	Intermediate Similarity	NPD6233	Phase 2
0.7219	Intermediate Similarity	NPD6663	Approved
0.7212	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1876	Approved
0.7208	Intermediate Similarity	NPD2799	Discontinued
0.7181	Intermediate Similarity	NPD5736	Approved
0.7175	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4140	Approved
0.717	Intermediate Similarity	NPD1511	Approved
0.7162	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD3226	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5735	Approved
0.7115	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD2346	Discontinued
0.7114	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD5844	Phase 1
0.7078	Intermediate Similarity	NPD4097	Suspended
0.7073	Intermediate Similarity	NPD6873	Phase 2
0.707	Intermediate Similarity	NPD4534	Discontinued
0.7065	Intermediate Similarity	NPD2494	Approved
0.7065	Intermediate Similarity	NPD2493	Approved
0.7062	Intermediate Similarity	NPD8434	Phase 2
0.7059	Intermediate Similarity	NPD2979	Phase 3
0.7051	Intermediate Similarity	NPD2438	Suspended
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1470	Approved
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7043	Intermediate Similarity	NPD4583	Approved
0.7043	Intermediate Similarity	NPD4582	Approved
0.7041	Intermediate Similarity	NPD7199	Phase 2
0.7039	Intermediate Similarity	NPD3764	Approved
0.7037	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3818	Discontinued
0.7034	Intermediate Similarity	NPD5691	Approved
0.7032	Intermediate Similarity	NPD7097	Phase 1
0.7027	Intermediate Similarity	NPD5327	Phase 3
0.702	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD447	Suspended
0.7012	Intermediate Similarity	NPD6599	Discontinued
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3092	Approved
0.7007	Intermediate Similarity	NPD1201	Approved
0.7006	Intermediate Similarity	NPD2344	Approved
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD3300	Phase 2
0.6993	Remote Similarity	NPD4198	Discontinued
0.6993	Remote Similarity	NPD4062	Phase 3
0.6993	Remote Similarity	NPD7157	Approved
0.6989	Remote Similarity	NPD4002	Approved
0.6989	Remote Similarity	NPD4004	Approved
0.6988	Remote Similarity	NPD1465	Phase 2
0.6982	Remote Similarity	NPD5494	Approved
0.6973	Remote Similarity	NPD3452	Approved
0.6973	Remote Similarity	NPD3450	Approved
0.6968	Remote Similarity	NPD6353	Approved
0.6966	Remote Similarity	NPD3091	Approved
0.6964	Remote Similarity	NPD7075	Discontinued
0.6962	Remote Similarity	NPD2424	Discontinued
0.6954	Remote Similarity	NPD7074	Phase 3
0.6954	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1613	Approved
0.6946	Remote Similarity	NPD5978	Approved
0.6946	Remote Similarity	NPD5977	Approved
0.6933	Remote Similarity	NPD3094	Phase 2
0.6932	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2898	Approved
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD1357	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6797	Phase 2
0.6909	Remote Similarity	NPD4380	Phase 2
0.6897	Remote Similarity	NPD7054	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1510	Phase 2
0.6879	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7685	Pre-registration
0.6875	Remote Similarity	NPD7251	Discontinued
0.6875	Remote Similarity	NPD7240	Approved
0.6875	Remote Similarity	NPD3750	Approved
0.6871	Remote Similarity	NPD5049	Phase 3
0.6871	Remote Similarity	NPD4059	Approved
0.686	Remote Similarity	NPD3926	Phase 2
0.6859	Remote Similarity	NPD1607	Approved
0.6857	Remote Similarity	NPD7472	Approved
0.6855	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5958	Discontinued
0.6853	Remote Similarity	NPD1241	Discontinued
0.6848	Remote Similarity	NPD2973	Approved
0.6848	Remote Similarity	NPD2975	Approved
0.6848	Remote Similarity	NPD2974	Approved
0.6846	Remote Similarity	NPD2233	Approved
0.6846	Remote Similarity	NPD2232	Approved
0.6846	Remote Similarity	NPD2230	Approved
0.6846	Remote Similarity	NPD1608	Approved
0.6839	Remote Similarity	NPD1240	Approved
0.6839	Remote Similarity	NPD3751	Discontinued
0.6836	Remote Similarity	NPD7808	Phase 3
0.6835	Remote Similarity	NPD2531	Phase 2
0.6832	Remote Similarity	NPD2309	Approved
0.6832	Remote Similarity	NPD2354	Approved
0.6828	Remote Similarity	NPD4580	Approved
0.6824	Remote Similarity	NPD3847	Discontinued
0.6818	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD5110	Phase 2
0.6818	Remote Similarity	NPD5109	Approved
0.6818	Remote Similarity	NPD5111	Phase 2
0.6818	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2629	Approved
0.6803	Remote Similarity	NPD5585	Approved
0.6802	Remote Similarity	NPD3787	Discontinued
0.6798	Remote Similarity	NPD2968	Approved
0.6798	Remote Similarity	NPD2971	Approved
0.6797	Remote Similarity	NPD4908	Phase 1
0.6795	Remote Similarity	NPD230	Phase 1
0.6786	Remote Similarity	NPD7819	Suspended
0.6776	Remote Similarity	NPD5647	Approved
0.6776	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2674	Phase 3
0.6772	Remote Similarity	NPD4308	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