NPASS Compound

Structure

CID220155 OpenBabel06191716012D 31 35 0 0 1 0 0 0 0 0999 V2000 2.0074 -2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4207 -0.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6120 -0.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2157 -0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 2.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8090 -1.8849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -2.6453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4726 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 0.6977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7405 -0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8144 -1.7804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.6977 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 -2.5235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 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 5 7 1 0 0 0 0 5 17 2 0 0 0 0 6 10 2 0 0 0 0 6 17 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 28 1 0 0 0 0 15 19 2 0 0 0 0 16 2 1 1 0 0 0 16 20 1 0 0 0 0 17 27 1 0 0 0 0 18 7 1 6 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 22 27 1 1 0 0 0 23 16 1 1 0 0 0 23 31 1 0 0 0 0 24 27 1 0 0 0 0 24 29 2 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.26
Volume:	454.744
LogP:	4.223
LogD:	3.772
LogS:	-4.498
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.662
Synthetic Accessibility Score:	5.117
Fsp3:	0.704
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:	-4.863
MDCK Permeability:	2.731594031502027e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.422
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.776
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.487
Plasma Protein Binding (PPB):	89.67444610595703%
Volume Distribution (VD):	0.962
Pgp-substrate:	3.5846338272094727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.332
CYP2C19-inhibitor:	0.611
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.874

ADMET: Excretion

Clearance (CL):	15.687
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.89
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.154
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.708
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.954
Carcinogencity:	0.735
Eye Corrosion:	0.013
Eye Irritation:	0.022
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC220155

Natural Product ID:	NPC220155
*Common Name:**	Withalongolide F
IUPAC Name:	(2R)-2-[(1S)-1-[(3aR,3bS,5aS,6R,8aS,8bS)-3a,5a-dimethyl-3-oxo-4,5,6,7,8,8a,8b,9-octahydro-3bH-indeno[5,4-e]inden-6-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:	withalongolide F
Standard InCHIKey:	IBYXDWNHLOGYIN-OSVRZWSTSA-N
Standard InCHI:	InChI=1S/C27H36O4/c1-15-13-23(31-25(30)19(15)14-28)16(2)20-8-9-21-18-7-5-17-6-10-24(29)27(17,4)22(18)11-12-26(20,21)3/h5-6,10,16,18,20-23,28H,7-9,11-14H2,1-4H3/t16-,18-,20+,21-,22-,23+,26+,27-/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934458
PubChem CID:	56926117
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[512837]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[512837]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[512837]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[512837]

☑ 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 NPC220155 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	189
0.1-0.2	922
0.2-0.3	3426
0.3-0.4	7548
0.4-0.5	13799
0.5-0.6	7841
0.6-0.7	6499
0.7-0.8	2278
0.8-0.85	172
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9327	High Similarity	NPC474315
0.9314	High Similarity	NPC91034
0.9048	High Similarity	NPC29133
0.8962	High Similarity	NPC470961
0.8879	High Similarity	NPC69291
0.8879	High Similarity	NPC191620
0.8796	High Similarity	NPC122056
0.8716	High Similarity	NPC147912
0.8716	High Similarity	NPC67259
0.8713	High Similarity	NPC202705
0.8667	High Similarity	NPC266570
0.8641	High Similarity	NPC99411
0.8641	High Similarity	NPC469657
0.8641	High Similarity	NPC244456
0.8627	High Similarity	NPC235464
0.8627	High Similarity	NPC98868
0.8627	High Similarity	NPC166745
0.86	High Similarity	NPC53685
0.8559	High Similarity	NPC140055
0.8559	High Similarity	NPC167606
0.8559	High Similarity	NPC286528
0.8559	High Similarity	NPC20302
0.8559	High Similarity	NPC183580
0.8559	High Similarity	NPC312824
0.8559	High Similarity	NPC470493
0.8558	High Similarity	NPC32577
0.8558	High Similarity	NPC114540
0.8558	High Similarity	NPC155332
0.8544	High Similarity	NPC474012
0.8544	High Similarity	NPC476299
0.8519	High Similarity	NPC37116
0.8515	High Similarity	NPC209355
0.8515	High Similarity	NPC171395
0.85	High Similarity	NPC115021
0.8491	Intermediate Similarity	NPC189863
0.8482	Intermediate Similarity	NPC50774
0.8482	Intermediate Similarity	NPC709
0.8476	Intermediate Similarity	NPC475526
0.8476	Intermediate Similarity	NPC473283
0.8476	Intermediate Similarity	NPC72151
0.8476	Intermediate Similarity	NPC329345
0.8468	Intermediate Similarity	NPC64318
0.8462	Intermediate Similarity	NPC115899
0.8462	Intermediate Similarity	NPC282524
0.8447	Intermediate Similarity	NPC471717
0.8447	Intermediate Similarity	NPC108368
0.8447	Intermediate Similarity	NPC57079
0.8426	Intermediate Similarity	NPC475065
0.8426	Intermediate Similarity	NPC137911
0.8426	Intermediate Similarity	NPC228477
0.8411	Intermediate Similarity	NPC330011
0.8411	Intermediate Similarity	NPC329048
0.8411	Intermediate Similarity	NPC473284
0.8411	Intermediate Similarity	NPC475294
0.8407	Intermediate Similarity	NPC264954
0.8396	Intermediate Similarity	NPC472868
0.8393	Intermediate Similarity	NPC470492
0.8393	Intermediate Similarity	NPC243065
0.8381	Intermediate Similarity	NPC320447
0.8378	Intermediate Similarity	NPC474181
0.8365	Intermediate Similarity	NPC227865
0.8365	Intermediate Similarity	NPC266955
0.8364	Intermediate Similarity	NPC236217
0.835	Intermediate Similarity	NPC156546
0.835	Intermediate Similarity	NPC208094
0.835	Intermediate Similarity	NPC53844
0.835	Intermediate Similarity	NPC2049
0.835	Intermediate Similarity	NPC476253
0.835	Intermediate Similarity	NPC253826
0.8333	Intermediate Similarity	NPC474370
0.8333	Intermediate Similarity	NPC318363
0.8333	Intermediate Similarity	NPC473482
0.8333	Intermediate Similarity	NPC476962
0.8333	Intermediate Similarity	NPC33473
0.8333	Intermediate Similarity	NPC475418
0.8319	Intermediate Similarity	NPC186525
0.8317	Intermediate Similarity	NPC229976
0.8302	Intermediate Similarity	NPC112009
0.8302	Intermediate Similarity	NPC475050
0.8286	Intermediate Similarity	NPC224720
0.8286	Intermediate Similarity	NPC476240
0.8286	Intermediate Similarity	NPC476223
0.8286	Intermediate Similarity	NPC310981
0.8286	Intermediate Similarity	NPC472924
0.8269	Intermediate Similarity	NPC316598
0.8269	Intermediate Similarity	NPC197386
0.8261	Intermediate Similarity	NPC67569
0.8261	Intermediate Similarity	NPC46570
0.8252	Intermediate Similarity	NPC301534
0.8252	Intermediate Similarity	NPC328371
0.8252	Intermediate Similarity	NPC190713
0.8252	Intermediate Similarity	NPC29152
0.8252	Intermediate Similarity	NPC471153
0.8252	Intermediate Similarity	NPC250757
0.8252	Intermediate Similarity	NPC472941
0.8252	Intermediate Similarity	NPC456
0.8241	Intermediate Similarity	NPC476958
0.823	Intermediate Similarity	NPC239273
0.823	Intermediate Similarity	NPC476959
0.8224	Intermediate Similarity	NPC294259
0.8218	Intermediate Similarity	NPC177037
0.8218	Intermediate Similarity	NPC204341
0.8218	Intermediate Similarity	NPC473986
0.8218	Intermediate Similarity	NPC190442
0.8218	Intermediate Similarity	NPC472814
0.8218	Intermediate Similarity	NPC474018
0.8208	Intermediate Similarity	NPC475320
0.8205	Intermediate Similarity	NPC8369
0.82	Intermediate Similarity	NPC5509
0.82	Intermediate Similarity	NPC474844
0.82	Intermediate Similarity	NPC177141
0.8198	Intermediate Similarity	NPC100267
0.8198	Intermediate Similarity	NPC475524
0.8198	Intermediate Similarity	NPC221144
0.819	Intermediate Similarity	NPC476274
0.819	Intermediate Similarity	NPC88326
0.819	Intermediate Similarity	NPC23786
0.819	Intermediate Similarity	NPC35751
0.819	Intermediate Similarity	NPC153700
0.819	Intermediate Similarity	NPC201406
0.819	Intermediate Similarity	NPC470265
0.819	Intermediate Similarity	NPC107493
0.8182	Intermediate Similarity	NPC473627
0.8173	Intermediate Similarity	NPC110937
0.8173	Intermediate Similarity	NPC141401
0.8173	Intermediate Similarity	NPC475894
0.8158	Intermediate Similarity	NPC475913
0.8155	Intermediate Similarity	NPC318282
0.8155	Intermediate Similarity	NPC469995
0.8155	Intermediate Similarity	NPC293052
0.8155	Intermediate Similarity	NPC88310
0.8155	Intermediate Similarity	NPC174948
0.8155	Intermediate Similarity	NPC476174
0.8155	Intermediate Similarity	NPC295347
0.8155	Intermediate Similarity	NPC173875
0.8142	Intermediate Similarity	NPC148458
0.8142	Intermediate Similarity	NPC476963
0.8137	Intermediate Similarity	NPC472942
0.8137	Intermediate Similarity	NPC474736
0.8131	Intermediate Similarity	NPC470954
0.8131	Intermediate Similarity	NPC183570
0.8131	Intermediate Similarity	NPC476237
0.8131	Intermediate Similarity	NPC180204
0.8131	Intermediate Similarity	NPC476889
0.812	Intermediate Similarity	NPC469789
0.8119	Intermediate Similarity	NPC469595
0.8119	Intermediate Similarity	NPC220454
0.8119	Intermediate Similarity	NPC477147
0.8119	Intermediate Similarity	NPC212679
0.8119	Intermediate Similarity	NPC477149
0.8119	Intermediate Similarity	NPC51486
0.8119	Intermediate Similarity	NPC273199
0.8113	Intermediate Similarity	NPC168319
0.8113	Intermediate Similarity	NPC194028
0.8095	Intermediate Similarity	NPC92275
0.8087	Intermediate Similarity	NPC474179
0.8087	Intermediate Similarity	NPC473270
0.8087	Intermediate Similarity	NPC473274
0.8087	Intermediate Similarity	NPC475834
0.8081	Intermediate Similarity	NPC194417
0.8077	Intermediate Similarity	NPC242848
0.8073	Intermediate Similarity	NPC472925
0.807	Intermediate Similarity	NPC476965
0.807	Intermediate Similarity	NPC470959
0.8058	Intermediate Similarity	NPC184870
0.8058	Intermediate Similarity	NPC469406
0.8058	Intermediate Similarity	NPC474690
0.8056	Intermediate Similarity	NPC309190
0.8056	Intermediate Similarity	NPC473175
0.8056	Intermediate Similarity	NPC189616
0.8056	Intermediate Similarity	NPC272632
0.8053	Intermediate Similarity	NPC470953
0.8051	Intermediate Similarity	NPC470494
0.8051	Intermediate Similarity	NPC3381
0.8051	Intermediate Similarity	NPC8374
0.8037	Intermediate Similarity	NPC31058
0.8037	Intermediate Similarity	NPC476890
0.8037	Intermediate Similarity	NPC469606
0.8037	Intermediate Similarity	NPC136289
0.8037	Intermediate Similarity	NPC40918
0.8037	Intermediate Similarity	NPC273005
0.8037	Intermediate Similarity	NPC473163
0.8036	Intermediate Similarity	NPC475970
0.8036	Intermediate Similarity	NPC285956
0.802	Intermediate Similarity	NPC174342
0.802	Intermediate Similarity	NPC262043
0.802	Intermediate Similarity	NPC474570
0.802	Intermediate Similarity	NPC214387
0.802	Intermediate Similarity	NPC284561
0.8019	Intermediate Similarity	NPC290802
0.8019	Intermediate Similarity	NPC287833
0.8019	Intermediate Similarity	NPC54705
0.8019	Intermediate Similarity	NPC477720
0.8019	Intermediate Similarity	NPC477521
0.8018	Intermediate Similarity	NPC179642
0.8018	Intermediate Similarity	NPC16270
0.8	Intermediate Similarity	NPC472825
0.8	Intermediate Similarity	NPC475709
0.8	Intermediate Similarity	NPC312561
0.8	Intermediate Similarity	NPC96496

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 NPC220155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1112
0.2-0.3	3255
0.3-0.4	2928
0.4-0.5	1074
0.5-0.6	289
0.6-0.7	231
0.7-0.8	99
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
0.8559	High Similarity	NPD7115	Discovery
0.7941	Intermediate Similarity	NPD5785	Approved
0.7864	Intermediate Similarity	NPD7637	Suspended
0.783	Intermediate Similarity	NPD6084	Phase 2
0.783	Intermediate Similarity	NPD6083	Phase 2
0.7788	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD6411	Approved
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7679	Intermediate Similarity	NPD6881	Approved
0.7679	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5695	Phase 3
0.7619	Intermediate Similarity	NPD5779	Approved
0.7619	Intermediate Similarity	NPD5778	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7589	Intermediate Similarity	NPD5697	Approved
0.7573	Intermediate Similarity	NPD5737	Approved
0.7573	Intermediate Similarity	NPD6672	Approved
0.7573	Intermediate Similarity	NPD6903	Approved
0.7565	Intermediate Similarity	NPD6053	Discontinued
0.7549	Intermediate Similarity	NPD7521	Approved
0.7549	Intermediate Similarity	NPD7334	Approved
0.7549	Intermediate Similarity	NPD5279	Phase 3
0.7549	Intermediate Similarity	NPD5330	Approved
0.7549	Intermediate Similarity	NPD6684	Approved
0.7549	Intermediate Similarity	NPD6409	Approved
0.7549	Intermediate Similarity	NPD7146	Approved
0.7544	Intermediate Similarity	NPD7290	Approved
0.7544	Intermediate Similarity	NPD6883	Approved
0.7544	Intermediate Similarity	NPD7102	Approved
0.7525	Intermediate Similarity	NPD4786	Approved
0.7524	Intermediate Similarity	NPD6079	Approved
0.7524	Intermediate Similarity	NPD5281	Approved
0.7524	Intermediate Similarity	NPD5284	Approved
0.7522	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6402	Approved
0.7478	Intermediate Similarity	NPD6650	Approved
0.7478	Intermediate Similarity	NPD6617	Approved
0.7478	Intermediate Similarity	NPD6869	Approved
0.7478	Intermediate Similarity	NPD6649	Approved
0.7478	Intermediate Similarity	NPD6847	Approved
0.7478	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6014	Approved
0.7456	Intermediate Similarity	NPD6012	Approved
0.7456	Intermediate Similarity	NPD6013	Approved
0.7451	Intermediate Similarity	NPD5363	Approved
0.7431	Intermediate Similarity	NPD5696	Approved
0.7429	Intermediate Similarity	NPD5207	Approved
0.7426	Intermediate Similarity	NPD5362	Discontinued
0.7414	Intermediate Similarity	NPD8297	Approved
0.7414	Intermediate Similarity	NPD6882	Approved
0.7404	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5211	Phase 2
0.7368	Intermediate Similarity	NPD6011	Approved
0.7358	Intermediate Similarity	NPD6050	Approved
0.7358	Intermediate Similarity	NPD5693	Phase 1
0.7358	Intermediate Similarity	NPD5694	Approved
0.7353	Intermediate Similarity	NPD3666	Approved
0.7353	Intermediate Similarity	NPD3665	Phase 1
0.7353	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD5328	Approved
0.7327	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD3667	Approved
0.7315	Intermediate Similarity	NPD4629	Approved
0.7315	Intermediate Similarity	NPD5210	Approved
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.7282	Intermediate Similarity	NPD1694	Approved
0.7281	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5692	Phase 3
0.7257	Intermediate Similarity	NPD5141	Approved
0.7248	Intermediate Similarity	NPD5222	Approved
0.7248	Intermediate Similarity	NPD5221	Approved
0.7248	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD7748	Approved
0.7217	Intermediate Similarity	NPD6686	Approved
0.7212	Intermediate Similarity	NPD3618	Phase 1
0.7207	Intermediate Similarity	NPD5285	Approved
0.7207	Intermediate Similarity	NPD4696	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.7207	Intermediate Similarity	NPD6404	Discontinued
0.7196	Intermediate Similarity	NPD7515	Phase 2
0.7182	Intermediate Similarity	NPD5173	Approved
0.7177	Intermediate Similarity	NPD7492	Approved
0.717	Intermediate Similarity	NPD6904	Approved
0.717	Intermediate Similarity	NPD6673	Approved
0.717	Intermediate Similarity	NPD6080	Approved
0.7157	Intermediate Similarity	NPD4269	Approved
0.7157	Intermediate Similarity	NPD5209	Approved
0.7157	Intermediate Similarity	NPD4270	Approved
0.7156	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6319	Approved
0.7131	Intermediate Similarity	NPD6054	Approved
0.712	Intermediate Similarity	NPD6616	Approved
0.7087	Intermediate Similarity	NPD7154	Phase 3
0.7083	Intermediate Similarity	NPD6868	Approved
0.708	Intermediate Similarity	NPD5224	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD4633	Approved
0.708	Intermediate Similarity	NPD5225	Approved
0.708	Intermediate Similarity	NPD7632	Discontinued
0.7073	Intermediate Similarity	NPD7503	Approved
0.7063	Intermediate Similarity	NPD7078	Approved
0.7049	Intermediate Similarity	NPD7101	Approved
0.7049	Intermediate Similarity	NPD7100	Approved
0.7048	Intermediate Similarity	NPD5786	Approved
0.7048	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5280	Approved
0.7048	Intermediate Similarity	NPD4623	Approved
0.7048	Intermediate Similarity	NPD4694	Approved
0.7048	Intermediate Similarity	NPD4519	Discontinued
0.7048	Intermediate Similarity	NPD5690	Phase 2
0.7034	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7902	Approved
0.7027	Intermediate Similarity	NPD4755	Approved
0.7019	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5175	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.7009	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6051	Approved
0.7008	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD4221	Approved
0.699	Remote Similarity	NPD4223	Phase 3
0.6983	Remote Similarity	NPD6412	Phase 2
0.6972	Remote Similarity	NPD4202	Approved
0.6967	Remote Similarity	NPD6335	Approved
0.6961	Remote Similarity	NPD4252	Approved
0.6953	Remote Similarity	NPD7319	Approved
0.6952	Remote Similarity	NPD5329	Approved
0.6949	Remote Similarity	NPD4634	Approved
0.6942	Remote Similarity	NPD6274	Approved
0.6937	Remote Similarity	NPD4697	Phase 3
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6923	Remote Similarity	NPD6695	Phase 3
0.6917	Remote Similarity	NPD4632	Approved
0.6916	Remote Similarity	NPD5208	Approved
0.6903	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD6008	Approved
0.6893	Remote Similarity	NPD5369	Approved
0.6887	Remote Similarity	NPD6098	Approved
0.6885	Remote Similarity	NPD6317	Approved
0.688	Remote Similarity	NPD5988	Approved
0.6857	Remote Similarity	NPD4197	Approved
0.6857	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3668	Phase 3
0.6855	Remote Similarity	NPD6059	Approved
0.685	Remote Similarity	NPD7507	Approved
0.6847	Remote Similarity	NPD5654	Approved
0.6846	Remote Similarity	NPD7260	Phase 2
0.6838	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6313	Approved
0.6829	Remote Similarity	NPD6314	Approved
0.68	Remote Similarity	NPD8039	Approved
0.68	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8293	Discontinued
0.6796	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4695	Discontinued
0.6792	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4730	Approved
0.678	Remote Similarity	NPD4729	Approved
0.6762	Remote Similarity	NPD5332	Approved
0.6762	Remote Similarity	NPD5331	Approved
0.6762	Remote Similarity	NPD4788	Approved
0.6759	Remote Similarity	NPD4518	Approved
0.6757	Remote Similarity	NPD5282	Discontinued
0.6757	Remote Similarity	NPD6001	Approved
0.6757	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7900	Approved
0.6748	Remote Similarity	NPD6009	Approved
0.6731	Remote Similarity	NPD4790	Discontinued
0.6729	Remote Similarity	NPD4689	Approved
0.6729	Remote Similarity	NPD5205	Approved
0.6729	Remote Similarity	NPD4693	Phase 3
0.6729	Remote Similarity	NPD4688	Approved
0.6729	Remote Similarity	NPD4138	Approved
0.6729	Remote Similarity	NPD4690	Approved
0.6727	Remote Similarity	NPD7983	Approved
0.6727	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD8035	Phase 2
0.6726	Remote Similarity	NPD5959	Approved
0.6723	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5733	Approved
0.67	Remote Similarity	NPD4687	Approved
0.67	Remote Similarity	NPD4058	Approved
0.6699	Remote Similarity	NPD6929	Approved
0.6699	Remote Similarity	NPD4195	Approved
0.6693	Remote Similarity	NPD7604	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