NPASS Compound

Structure

NPC272656 OpenBabel07101718192D 31 38 0 0 1 0 0 0 0 0999 V2000 0.1359 2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7802 0.1758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7266 2.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3172 1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3419 0.0548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8006 0.6299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8642 1.4301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1796 1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0915 0.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4111 1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4686 0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2738 1.2329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3749 0.7897 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6369 0.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7366 0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4686 3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3347 1.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0556 1.8564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8797 1.6584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 -0.7728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6904 0.8436 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 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 30 1 0 0 0 0 12 16 2 0 0 0 0 12 29 1 0 0 0 0 13 21 1 1 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 23 1 6 0 0 0 20 28 1 0 0 0 0 21 27 1 1 0 0 0 22 15 1 1 0 0 0 22 29 1 0 0 0 0 22 31 1 0 0 0 0 23 16 1 6 0 0 0 23 30 1 0 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.1
Volume:	389.779
LogP:	1.732
LogD:	1.392
LogS:	-4.517
# Rotatable Bonds:	0
TPSA:	117.98
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	6.514
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.535
MDCK Permeability:	1.5982677723513916e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.32
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.574
Plasma Protein Binding (PPB):	79.7846908569336%
Volume Distribution (VD):	1.041
Pgp-substrate:	6.5932087898254395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.155
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	5.562
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.651
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.968
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.37
Skin Sensitization:	0.903
Carcinogencity:	0.78
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.397

Download Data

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

Natural Product: NPC272656

Natural Product ID:	NPC272656
*Common Name:**	PGWYTUHCGYSVOJ-VICRBMHYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PGWYTUHCGYSVOJ-VICRBMHYSA-N
Standard InCHI:	InChI=1S/C23H18O8/c24-10-6-7-12-16-14(10)17(25)18-20(28-18)23(16)30-11-4-1-3-9-15(11)22(29-12,31-23)13-5-2-8-21(13,27)19(9)26/h1,3-4,6-7,13,17-18,20,24-25,27H,2,5,8H2/t13-,17-,18-,20-,21+,22-,23+/m1/s1
SMILES:	Oc1ccc2c3c1[C@@H](O)[C@H]1O[C@H]1[C@@]13Oc3c4[C@](O2)(O1)[C@@H]1CCC[C@]1(C(=O)c4ccc3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487723
PubChem CID:	24899656
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32546	ymf 1.01029	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18479163]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	57.8	%	PMID[527286]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	46.8	%	PMID[527286]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	74.3	%	PMID[527286]
NPT593	Organism	Bursaphelenchus xylophilus	Bursaphelenchus xylophilus	Activity	=	58.3	%	PMID[527286]

☑ 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 NPC272656 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	440
0.1-0.2	1587
0.2-0.3	3168
0.3-0.4	7525
0.4-0.5	10496
0.5-0.6	5225
0.6-0.7	6977
0.7-0.8	7181
0.8-0.85	87
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9202	High Similarity	NPC183402
0.9085	High Similarity	NPC193749
0.9048	High Similarity	NPC103633
0.9042	High Similarity	NPC297404
0.9042	High Similarity	NPC11608
0.8994	High Similarity	NPC137460
0.8655	High Similarity	NPC472150
0.8529	High Similarity	NPC472153
0.8466	Intermediate Similarity	NPC3718
0.8448	Intermediate Similarity	NPC222455
0.8439	Intermediate Similarity	NPC175082
0.8436	Intermediate Similarity	NPC186746
0.843	Intermediate Similarity	NPC74371
0.843	Intermediate Similarity	NPC120677
0.8421	Intermediate Similarity	NPC73148
0.8421	Intermediate Similarity	NPC478222
0.8421	Intermediate Similarity	NPC316457
0.8418	Intermediate Similarity	NPC102053
0.8418	Intermediate Similarity	NPC475246
0.8412	Intermediate Similarity	NPC472156
0.8409	Intermediate Similarity	NPC470438
0.8405	Intermediate Similarity	NPC23807
0.84	Intermediate Similarity	NPC8704
0.84	Intermediate Similarity	NPC313304
0.84	Intermediate Similarity	NPC241874
0.84	Intermediate Similarity	NPC287884
0.8391	Intermediate Similarity	NPC225419
0.8382	Intermediate Similarity	NPC75944
0.838	Intermediate Similarity	NPC315221
0.838	Intermediate Similarity	NPC208069
0.8372	Intermediate Similarity	NPC278329
0.8372	Intermediate Similarity	NPC101116
0.8372	Intermediate Similarity	NPC478229
0.8372	Intermediate Similarity	NPC146837
0.8372	Intermediate Similarity	NPC212099
0.8372	Intermediate Similarity	NPC473961
0.8353	Intermediate Similarity	NPC177742
0.8352	Intermediate Similarity	NPC294501
0.8343	Intermediate Similarity	NPC246274
0.8333	Intermediate Similarity	NPC313452
0.8324	Intermediate Similarity	NPC153578
0.8324	Intermediate Similarity	NPC127415
0.8324	Intermediate Similarity	NPC314687
0.8324	Intermediate Similarity	NPC114257
0.8324	Intermediate Similarity	NPC299149
0.8324	Intermediate Similarity	NPC244903
0.8324	Intermediate Similarity	NPC277710
0.8324	Intermediate Similarity	NPC58538
0.8323	Intermediate Similarity	NPC475890
0.8315	Intermediate Similarity	NPC475233
0.8315	Intermediate Similarity	NPC156635
0.8315	Intermediate Similarity	NPC46958
0.8315	Intermediate Similarity	NPC66820
0.8315	Intermediate Similarity	NPC76112
0.8315	Intermediate Similarity	NPC170018
0.8315	Intermediate Similarity	NPC92403
0.8306	Intermediate Similarity	NPC314672
0.8305	Intermediate Similarity	NPC154986
0.8305	Intermediate Similarity	NPC85368
0.8305	Intermediate Similarity	NPC203751
0.8304	Intermediate Similarity	NPC57072
0.8304	Intermediate Similarity	NPC231475
0.8295	Intermediate Similarity	NPC472160
0.8295	Intermediate Similarity	NPC478021
0.8289	Intermediate Similarity	NPC131405
0.8286	Intermediate Similarity	NPC63470
0.8278	Intermediate Similarity	NPC477860
0.8278	Intermediate Similarity	NPC475161
0.8278	Intermediate Similarity	NPC53680
0.8278	Intermediate Similarity	NPC208797
0.8276	Intermediate Similarity	NPC478020
0.8276	Intermediate Similarity	NPC472049
0.8276	Intermediate Similarity	NPC178281
0.8276	Intermediate Similarity	NPC478022
0.8276	Intermediate Similarity	NPC280923
0.827	Intermediate Similarity	NPC314020
0.8268	Intermediate Similarity	NPC47191
0.8268	Intermediate Similarity	NPC67302
0.8266	Intermediate Similarity	NPC56735
0.8266	Intermediate Similarity	NPC61594
0.8258	Intermediate Similarity	NPC472158
0.8258	Intermediate Similarity	NPC470667
0.8256	Intermediate Similarity	NPC284495
0.8249	Intermediate Similarity	NPC121333
0.8249	Intermediate Similarity	NPC257667
0.8249	Intermediate Similarity	NPC315619
0.8249	Intermediate Similarity	NPC186847
0.8249	Intermediate Similarity	NPC472454
0.8249	Intermediate Similarity	NPC76128
0.8249	Intermediate Similarity	NPC30432
0.8249	Intermediate Similarity	NPC5029
0.8249	Intermediate Similarity	NPC111536
0.8249	Intermediate Similarity	NPC271385
0.8246	Intermediate Similarity	NPC474398
0.8246	Intermediate Similarity	NPC476026
0.8246	Intermediate Similarity	NPC474441
0.8246	Intermediate Similarity	NPC474401
0.8246	Intermediate Similarity	NPC477833
0.8242	Intermediate Similarity	NPC87583
0.8232	Intermediate Similarity	NPC476203
0.8232	Intermediate Similarity	NPC478001
0.8232	Intermediate Similarity	NPC473883
0.8229	Intermediate Similarity	NPC178173
0.8229	Intermediate Similarity	NPC475174
0.8222	Intermediate Similarity	NPC254588
0.8218	Intermediate Similarity	NPC63438
0.8218	Intermediate Similarity	NPC121290
0.8218	Intermediate Similarity	NPC147596
0.8218	Intermediate Similarity	NPC475183
0.8214	Intermediate Similarity	NPC93619
0.8212	Intermediate Similarity	NPC289876
0.8202	Intermediate Similarity	NPC470336
0.8202	Intermediate Similarity	NPC199357
0.8202	Intermediate Similarity	NPC470335
0.8202	Intermediate Similarity	NPC98776
0.8198	Intermediate Similarity	NPC186113
0.8198	Intermediate Similarity	NPC226287
0.8197	Intermediate Similarity	NPC105591
0.8192	Intermediate Similarity	NPC74559
0.8192	Intermediate Similarity	NPC103307
0.8192	Intermediate Similarity	NPC34287
0.8192	Intermediate Similarity	NPC280385
0.8192	Intermediate Similarity	NPC471416
0.8192	Intermediate Similarity	NPC44558
0.8187	Intermediate Similarity	NPC292706
0.8187	Intermediate Similarity	NPC224557
0.8177	Intermediate Similarity	NPC170203
0.8177	Intermediate Similarity	NPC8940
0.8176	Intermediate Similarity	NPC478218
0.8171	Intermediate Similarity	NPC234052
0.8171	Intermediate Similarity	NPC329647
0.8171	Intermediate Similarity	NPC470735
0.8167	Intermediate Similarity	NPC476622
0.8167	Intermediate Similarity	NPC476620
0.8167	Intermediate Similarity	NPC476618
0.8167	Intermediate Similarity	NPC476623
0.8167	Intermediate Similarity	NPC477683
0.8167	Intermediate Similarity	NPC472387
0.8167	Intermediate Similarity	NPC477682
0.8167	Intermediate Similarity	NPC476621
0.8167	Intermediate Similarity	NPC476619
0.8166	Intermediate Similarity	NPC207346
0.8166	Intermediate Similarity	NPC46564
0.8162	Intermediate Similarity	NPC48474
0.8156	Intermediate Similarity	NPC193377
0.8156	Intermediate Similarity	NPC98667
0.8156	Intermediate Similarity	NPC86809
0.8156	Intermediate Similarity	NPC232412
0.8156	Intermediate Similarity	NPC186800
0.8156	Intermediate Similarity	NPC68381
0.8156	Intermediate Similarity	NPC108202
0.8156	Intermediate Similarity	NPC294149
0.8152	Intermediate Similarity	NPC205721
0.8152	Intermediate Similarity	NPC119094
0.8152	Intermediate Similarity	NPC7839
0.8152	Intermediate Similarity	NPC173872
0.8152	Intermediate Similarity	NPC142291
0.815	Intermediate Similarity	NPC471976
0.815	Intermediate Similarity	NPC271479
0.815	Intermediate Similarity	NPC328093
0.8146	Intermediate Similarity	NPC267254
0.8146	Intermediate Similarity	NPC262580
0.8146	Intermediate Similarity	NPC289396
0.8146	Intermediate Similarity	NPC81332
0.8146	Intermediate Similarity	NPC271848
0.8146	Intermediate Similarity	NPC472620
0.8146	Intermediate Similarity	NPC212038
0.8146	Intermediate Similarity	NPC301683
0.8144	Intermediate Similarity	NPC140722
0.8144	Intermediate Similarity	NPC92054
0.8144	Intermediate Similarity	NPC4958
0.8136	Intermediate Similarity	NPC326877
0.8136	Intermediate Similarity	NPC177480
0.8136	Intermediate Similarity	NPC472383
0.8136	Intermediate Similarity	NPC242395
0.8136	Intermediate Similarity	NPC112755
0.8136	Intermediate Similarity	NPC152477
0.8136	Intermediate Similarity	NPC471457
0.8136	Intermediate Similarity	NPC472381
0.8136	Intermediate Similarity	NPC170675
0.8132	Intermediate Similarity	NPC132111
0.8132	Intermediate Similarity	NPC150977
0.8129	Intermediate Similarity	NPC314257
0.8125	Intermediate Similarity	NPC70441
0.8122	Intermediate Similarity	NPC84494
0.8122	Intermediate Similarity	NPC245059
0.8122	Intermediate Similarity	NPC212290
0.8121	Intermediate Similarity	NPC472155
0.8118	Intermediate Similarity	NPC314459
0.8118	Intermediate Similarity	NPC253904
0.8118	Intermediate Similarity	NPC321363
0.8118	Intermediate Similarity	NPC470199
0.8118	Intermediate Similarity	NPC478220
0.8114	Intermediate Similarity	NPC17432
0.8114	Intermediate Similarity	NPC290160
0.8114	Intermediate Similarity	NPC214279
0.8111	Intermediate Similarity	NPC469345
0.8111	Intermediate Similarity	NPC314489
0.8111	Intermediate Similarity	NPC324220
0.8111	Intermediate Similarity	NPC297574

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 NPC272656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	871
0.2-0.3	1799
0.3-0.4	2672
0.4-0.5	1963
0.5-0.6	965
0.6-0.7	390
0.7-0.8	110
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8398	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD3751	Discontinued
0.8372	Intermediate Similarity	NPD3787	Discontinued
0.8315	Intermediate Similarity	NPD8312	Approved
0.8315	Intermediate Similarity	NPD8313	Approved
0.8085	Intermediate Similarity	NPD6782	Approved
0.8085	Intermediate Similarity	NPD6780	Approved
0.8085	Intermediate Similarity	NPD6777	Approved
0.8085	Intermediate Similarity	NPD6776	Approved
0.8085	Intermediate Similarity	NPD6781	Approved
0.8085	Intermediate Similarity	NPD6778	Approved
0.8085	Intermediate Similarity	NPD6779	Approved
0.8045	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD6166	Phase 2
0.7958	Intermediate Similarity	NPD7698	Approved
0.7958	Intermediate Similarity	NPD7697	Approved
0.7958	Intermediate Similarity	NPD7435	Discontinued
0.7958	Intermediate Similarity	NPD7696	Phase 3
0.7956	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6797	Phase 2
0.7933	Intermediate Similarity	NPD5844	Phase 1
0.7933	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD5402	Approved
0.7901	Intermediate Similarity	NPD7251	Discontinued
0.7889	Intermediate Similarity	NPD7074	Phase 3
0.7887	Intermediate Similarity	NPD7701	Phase 2
0.7877	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD7228	Approved
0.7874	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7808	Phase 3
0.7833	Intermediate Similarity	NPD7054	Approved
0.7824	Intermediate Similarity	NPD7871	Phase 2
0.7824	Intermediate Similarity	NPD7870	Phase 2
0.7819	Intermediate Similarity	NPD6534	Approved
0.7819	Intermediate Similarity	NPD6535	Approved
0.7812	Intermediate Similarity	NPD6823	Phase 2
0.7802	Intermediate Similarity	NPD7685	Pre-registration
0.7802	Intermediate Similarity	NPD6559	Discontinued
0.7797	Intermediate Similarity	NPD6959	Discontinued
0.7796	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7472	Approved
0.7789	Intermediate Similarity	NPD7700	Phase 2
0.7789	Intermediate Similarity	NPD7699	Phase 2
0.7766	Intermediate Similarity	NPD7801	Approved
0.774	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7874	Approved
0.7701	Intermediate Similarity	NPD37	Approved
0.7688	Intermediate Similarity	NPD4380	Phase 2
0.7688	Intermediate Similarity	NPD8150	Discontinued
0.7684	Intermediate Similarity	NPD6234	Discontinued
0.767	Intermediate Similarity	NPD4967	Phase 2
0.767	Intermediate Similarity	NPD4965	Approved
0.767	Intermediate Similarity	NPD4966	Approved
0.7661	Intermediate Similarity	NPD6273	Approved
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.763	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7075	Discontinued
0.7611	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7199	Phase 2
0.7594	Intermediate Similarity	NPD8434	Phase 2
0.7557	Intermediate Similarity	NPD1465	Phase 2
0.7557	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8320	Phase 1
0.7551	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.7514	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1934	Approved
0.7472	Intermediate Similarity	NPD3882	Suspended
0.7471	Intermediate Similarity	NPD3750	Approved
0.7458	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD2801	Approved
0.7458	Intermediate Similarity	NPD7819	Suspended
0.7432	Intermediate Similarity	NPD7473	Discontinued
0.7424	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7783	Phase 2
0.7413	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8127	Discontinued
0.7401	Intermediate Similarity	NPD6801	Discontinued
0.74	Intermediate Similarity	NPD8151	Discontinued
0.7399	Intermediate Similarity	NPD5401	Approved
0.7363	Intermediate Similarity	NPD6232	Discontinued
0.7343	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3749	Approved
0.733	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD3226	Approved
0.7326	Intermediate Similarity	NPD6190	Approved
0.7318	Intermediate Similarity	NPD3817	Phase 2
0.7306	Intermediate Similarity	NPD6213	Phase 3
0.7306	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6212	Phase 3
0.7299	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5762	Approved
0.7294	Intermediate Similarity	NPD5763	Approved
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7257	Intermediate Similarity	NPD1512	Approved
0.7256	Intermediate Similarity	NPD2861	Phase 2
0.7251	Intermediate Similarity	NPD1549	Phase 2
0.7247	Intermediate Similarity	NPD7411	Suspended
0.72	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7193	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6599	Discontinued
0.7182	Intermediate Similarity	NPD7768	Phase 2
0.7176	Intermediate Similarity	NPD3748	Approved
0.7168	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5761	Phase 2
0.7167	Intermediate Similarity	NPD5760	Phase 2
0.7143	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7135	Intermediate Similarity	NPD2935	Discontinued
0.7121	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7097	Phase 1
0.711	Intermediate Similarity	NPD6674	Discontinued
0.711	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8059	Phase 3
0.7069	Intermediate Similarity	NPD7003	Approved
0.7065	Intermediate Similarity	NPD7680	Approved
0.7041	Intermediate Similarity	NPD1613	Approved
0.7041	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD6099	Approved
0.7035	Intermediate Similarity	NPD6100	Approved
0.7024	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD7028	Phase 2
0.6994	Remote Similarity	NPD7266	Discontinued
0.6982	Remote Similarity	NPD6233	Phase 2
0.698	Remote Similarity	NPD7497	Discontinued
0.6977	Remote Similarity	NPD1510	Phase 2
0.6971	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6764	Approved
0.6963	Remote Similarity	NPD6765	Approved
0.6949	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1551	Phase 2
0.6936	Remote Similarity	NPD2796	Approved
0.6935	Remote Similarity	NPD1247	Approved
0.6931	Remote Similarity	NPD7799	Discontinued
0.6923	Remote Similarity	NPD6798	Discontinued
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4111	Phase 1
0.691	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4908	Phase 1
0.6897	Remote Similarity	NPD6004	Phase 3
0.6897	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6005	Phase 3
0.6897	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD4002	Approved
0.6897	Remote Similarity	NPD4004	Approved
0.6893	Remote Similarity	NPD7236	Approved
0.689	Remote Similarity	NPD7930	Approved
0.6879	Remote Similarity	NPD2799	Discontinued
0.6875	Remote Similarity	NPD8166	Discontinued
0.6869	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8285	Discontinued
0.6864	Remote Similarity	NPD4625	Phase 3
0.6863	Remote Similarity	NPD4582	Approved
0.6863	Remote Similarity	NPD4583	Approved
0.6862	Remote Similarity	NPD3926	Phase 2
0.6857	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2424	Discontinued
0.6854	Remote Similarity	NPD7390	Discontinued
0.6842	Remote Similarity	NPD4140	Approved
0.6842	Remote Similarity	NPD7177	Discontinued
0.684	Remote Similarity	NPD4665	Approved
0.6839	Remote Similarity	NPD5405	Approved
0.6839	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD5406	Approved
0.6839	Remote Similarity	NPD5408	Approved
0.6831	Remote Similarity	NPD6844	Discontinued
0.6828	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1470	Approved
0.6825	Remote Similarity	NPD8404	Phase 2
0.6824	Remote Similarity	NPD2313	Discontinued
0.6821	Remote Similarity	NPD6784	Approved
0.6821	Remote Similarity	NPD6785	Approved
0.6818	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7229	Phase 3
0.6806	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5735	Approved
0.6802	Remote Similarity	NPD1933	Approved
0.68	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2493	Approved
0.6798	Remote Similarity	NPD3300	Phase 2

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