NPASS Compound

Structure

NPC471483 OpenBabel07101718252D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.6714 2.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3017 1.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3951 -0.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6413 2.1470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1613 2.0538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7522 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8357 1.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0517 2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8357 3.3775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 1.7457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8357 1.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3207 0.9650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8357 1.1748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3462 1.6644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8357 0.4825 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8357 1.1748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8357 0.4825 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8357 4.3425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2857 0.9650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6188 1.9134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6067 0.5945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9956 2.8641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8950 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 0.1843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3462 1.6644 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 9 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 19 2 0 0 0 0 9 24 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 1 0 0 0 13 20 2 0 0 0 0 13 25 1 0 0 0 0 14 15 1 6 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 2 1 6 0 0 0 15 26 1 0 0 0 0 16 3 1 6 0 0 0 16 27 1 0 0 0 0 17 16 1 1 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 12 1 6 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.14
Volume:	356.861
LogP:	1.11
LogD:	0.46
LogS:	-3.539
# Rotatable Bonds:	4
TPSA:	120.75
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	6.638
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337
MDCK Permeability:	6.78995274938643e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.471
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.405
Plasma Protein Binding (PPB):	25.12384033203125%
Volume Distribution (VD):	0.794
Pgp-substrate:	62.34724044799805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	4.08
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.337
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.962
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.407
Skin Sensitization:	0.551
Carcinogencity:	0.859
Eye Corrosion:	0.004
Eye Irritation:	0.019
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC471483

Natural Product ID:	NPC471483
*Common Name:**	Spicatolide G
IUPAC Name:	n.a.
Synonyms:	spicatolide G
Standard InCHIKey:	UKTJRGULNRJYPT-IPPTUDOFSA-N
Standard InCHI:	InChI=1S/C18H24O9/c1-9(19)24-11-7-16(3)17(22)6-5-15(2,26-17)14(21)18(27-16)12(11)10(8-23-4)13(20)25-18/h11,14,21-22H,5-8H2,1-4H3/t11-,14+,15+,16+,17-,18+/m0/s1
SMILES:	COCC1=C2[C@@H](OC(=O)C)C[C@]3(O[C@@]2(OC1=O)[C@H](O)[C@@]1(C)CC[C@@]3(O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252712
PubChem CID:	44445361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001818] Furopyrans

*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
NPO32710	pseudoelephantopus spicatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17970595]

☑ 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	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[536436]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4.8	ug.mL-1	PMID[536436]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[536436]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[536436]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.1	ug.mL-1	PMID[536436]

☑ 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 NPC471483 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	201
0.1-0.2	1497
0.2-0.3	5397
0.3-0.4	12325
0.4-0.5	11775
0.5-0.6	7345
0.6-0.7	3789
0.7-0.8	352
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8526	High Similarity	NPC2666
0.8511	High Similarity	NPC471492
0.8421	Intermediate Similarity	NPC473333
0.8333	Intermediate Similarity	NPC471490
0.8144	Intermediate Similarity	NPC218064
0.8085	Intermediate Similarity	NPC118078
0.8021	Intermediate Similarity	NPC256368
0.8	Intermediate Similarity	NPC158061
0.7941	Intermediate Similarity	NPC239961
0.7917	Intermediate Similarity	NPC472195
0.7917	Intermediate Similarity	NPC472196
0.7917	Intermediate Similarity	NPC238090
0.7895	Intermediate Similarity	NPC471184
0.7857	Intermediate Similarity	NPC98165
0.7849	Intermediate Similarity	NPC311163
0.7835	Intermediate Similarity	NPC471496
0.7835	Intermediate Similarity	NPC159698
0.7822	Intermediate Similarity	NPC313569
0.7812	Intermediate Similarity	NPC470520
0.7778	Intermediate Similarity	NPC199099
0.7778	Intermediate Similarity	NPC266842
0.7766	Intermediate Similarity	NPC475037
0.7755	Intermediate Similarity	NPC473334
0.7742	Intermediate Similarity	NPC471494
0.7723	Intermediate Similarity	NPC198992
0.7708	Intermediate Similarity	NPC3436
0.7708	Intermediate Similarity	NPC177668
0.77	Intermediate Similarity	NPC187268
0.77	Intermediate Similarity	NPC203627
0.767	Intermediate Similarity	NPC474917
0.767	Intermediate Similarity	NPC161775
0.766	Intermediate Similarity	NPC204048
0.7653	Intermediate Similarity	NPC470521
0.7653	Intermediate Similarity	NPC472198
0.7647	Intermediate Similarity	NPC121423
0.7629	Intermediate Similarity	NPC175842
0.7629	Intermediate Similarity	NPC32494
0.7629	Intermediate Similarity	NPC9447
0.7629	Intermediate Similarity	NPC472199
0.7619	Intermediate Similarity	NPC475960
0.7604	Intermediate Similarity	NPC225283
0.7604	Intermediate Similarity	NPC133450
0.76	Intermediate Similarity	NPC471462
0.7596	Intermediate Similarity	NPC85670
0.7576	Intermediate Similarity	NPC220221
0.7553	Intermediate Similarity	NPC475034
0.7553	Intermediate Similarity	NPC470124
0.7551	Intermediate Similarity	NPC156553
0.7551	Intermediate Similarity	NPC320089
0.7551	Intermediate Similarity	NPC473561
0.7551	Intermediate Similarity	NPC59646
0.7551	Intermediate Similarity	NPC473723
0.7551	Intermediate Similarity	NPC473663
0.7551	Intermediate Similarity	NPC475173
0.7547	Intermediate Similarity	NPC257853
0.7526	Intermediate Similarity	NPC471569
0.7526	Intermediate Similarity	NPC202886
0.7525	Intermediate Similarity	NPC472015
0.75	Intermediate Similarity	NPC100487
0.75	Intermediate Similarity	NPC306041
0.75	Intermediate Similarity	NPC472748
0.75	Intermediate Similarity	NPC143446
0.7451	Intermediate Similarity	NPC130792
0.7449	Intermediate Similarity	NPC477749
0.7447	Intermediate Similarity	NPC16887
0.7447	Intermediate Similarity	NPC53011
0.7447	Intermediate Similarity	NPC37005
0.7447	Intermediate Similarity	NPC154893
0.7447	Intermediate Similarity	NPC475035
0.7431	Intermediate Similarity	NPC264153
0.7429	Intermediate Similarity	NPC472749
0.7429	Intermediate Similarity	NPC82251
0.7429	Intermediate Similarity	NPC472751
0.7426	Intermediate Similarity	NPC40812
0.7426	Intermediate Similarity	NPC236580
0.7426	Intermediate Similarity	NPC304445
0.7423	Intermediate Similarity	NPC242877
0.7423	Intermediate Similarity	NPC64913
0.7423	Intermediate Similarity	NPC477748
0.7404	Intermediate Similarity	NPC475945
0.7404	Intermediate Similarity	NPC472750
0.7404	Intermediate Similarity	NPC472747
0.7404	Intermediate Similarity	NPC309398
0.7404	Intermediate Similarity	NPC473070
0.7404	Intermediate Similarity	NPC475871
0.74	Intermediate Similarity	NPC36954
0.74	Intermediate Similarity	NPC471141
0.7383	Intermediate Similarity	NPC315836
0.7383	Intermediate Similarity	NPC313668
0.7383	Intermediate Similarity	NPC206618
0.7374	Intermediate Similarity	NPC475912
0.7374	Intermediate Similarity	NPC476300
0.7374	Intermediate Similarity	NPC81419
0.7374	Intermediate Similarity	NPC179746
0.7374	Intermediate Similarity	NPC473520
0.7358	Intermediate Similarity	NPC26617
0.7358	Intermediate Similarity	NPC254538
0.7358	Intermediate Similarity	NPC474285
0.7353	Intermediate Similarity	NPC249171
0.7353	Intermediate Similarity	NPC471144
0.7353	Intermediate Similarity	NPC222303
0.7353	Intermediate Similarity	NPC473326
0.7353	Intermediate Similarity	NPC49833
0.7347	Intermediate Similarity	NPC473904
0.7347	Intermediate Similarity	NPC206614
0.7347	Intermediate Similarity	NPC474323
0.734	Intermediate Similarity	NPC27314
0.734	Intermediate Similarity	NPC31019
0.734	Intermediate Similarity	NPC263087
0.734	Intermediate Similarity	NPC106912
0.734	Intermediate Similarity	NPC2379
0.7333	Intermediate Similarity	NPC203659
0.7333	Intermediate Similarity	NPC473068
0.7327	Intermediate Similarity	NPC54731
0.7327	Intermediate Similarity	NPC288350
0.7327	Intermediate Similarity	NPC279621
0.7327	Intermediate Similarity	NPC230800
0.7327	Intermediate Similarity	NPC173329
0.7327	Intermediate Similarity	NPC472995
0.7321	Intermediate Similarity	NPC475309
0.732	Intermediate Similarity	NPC233551
0.732	Intermediate Similarity	NPC40376
0.732	Intermediate Similarity	NPC48338
0.732	Intermediate Similarity	NPC20339
0.732	Intermediate Similarity	NPC21208
0.732	Intermediate Similarity	NPC280621
0.7315	Intermediate Similarity	NPC235014
0.7308	Intermediate Similarity	NPC201191
0.7308	Intermediate Similarity	NPC86077
0.7308	Intermediate Similarity	NPC472754
0.7308	Intermediate Similarity	NPC149371
0.7308	Intermediate Similarity	NPC474747
0.7304	Intermediate Similarity	NPC186339
0.73	Intermediate Similarity	NPC71589
0.73	Intermediate Similarity	NPC474338
0.7297	Intermediate Similarity	NPC277583
0.729	Intermediate Similarity	NPC219900
0.729	Intermediate Similarity	NPC392
0.729	Intermediate Similarity	NPC177524
0.729	Intermediate Similarity	NPC38948
0.7282	Intermediate Similarity	NPC288876
0.7282	Intermediate Similarity	NPC473146
0.7273	Intermediate Similarity	NPC208886
0.7273	Intermediate Similarity	NPC287075
0.7273	Intermediate Similarity	NPC30515
0.7273	Intermediate Similarity	NPC12172
0.7273	Intermediate Similarity	NPC184463
0.7273	Intermediate Similarity	NPC472197
0.7264	Intermediate Similarity	NPC476738
0.7264	Intermediate Similarity	NPC476740
0.7263	Intermediate Similarity	NPC266718
0.7263	Intermediate Similarity	NPC290052
0.7255	Intermediate Similarity	NPC472998
0.7245	Intermediate Similarity	NPC130359
0.7245	Intermediate Similarity	NPC139418
0.7245	Intermediate Similarity	NPC14901
0.7238	Intermediate Similarity	NPC474581
0.7238	Intermediate Similarity	NPC159533
0.7238	Intermediate Similarity	NPC473148
0.7238	Intermediate Similarity	NPC110989
0.7238	Intermediate Similarity	NPC69171
0.7238	Intermediate Similarity	NPC474165
0.7238	Intermediate Similarity	NPC473816
0.7238	Intermediate Similarity	NPC472755
0.7238	Intermediate Similarity	NPC475367
0.7238	Intermediate Similarity	NPC4620
0.7234	Intermediate Similarity	NPC310450
0.7234	Intermediate Similarity	NPC11383
0.7234	Intermediate Similarity	NPC474959
0.7234	Intermediate Similarity	NPC475046
0.7228	Intermediate Similarity	NPC469873
0.7228	Intermediate Similarity	NPC304886
0.7228	Intermediate Similarity	NPC270013
0.7228	Intermediate Similarity	NPC471142
0.7228	Intermediate Similarity	NPC227494
0.7228	Intermediate Similarity	NPC14961
0.7222	Intermediate Similarity	NPC38154
0.7216	Intermediate Similarity	NPC178215
0.7212	Intermediate Similarity	NPC4637
0.7212	Intermediate Similarity	NPC150923
0.7212	Intermediate Similarity	NPC474339
0.7212	Intermediate Similarity	NPC472753
0.7212	Intermediate Similarity	NPC219038
0.7212	Intermediate Similarity	NPC473332
0.7212	Intermediate Similarity	NPC474742
0.7212	Intermediate Similarity	NPC47880
0.7212	Intermediate Similarity	NPC67296
0.7212	Intermediate Similarity	NPC98859
0.7212	Intermediate Similarity	NPC164598
0.7207	Intermediate Similarity	NPC106446
0.72	Intermediate Similarity	NPC212486
0.72	Intermediate Similarity	NPC472641
0.72	Intermediate Similarity	NPC110022
0.72	Intermediate Similarity	NPC189651
0.72	Intermediate Similarity	NPC475098
0.72	Intermediate Similarity	NPC472640
0.7196	Intermediate Similarity	NPC477513
0.7188	Intermediate Similarity	NPC471567
0.7188	Intermediate Similarity	NPC329615
0.7188	Intermediate Similarity	NPC477014

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 NPC471483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2017
0.2-0.3	3952
0.3-0.4	2097
0.4-0.5	631
0.5-0.6	226
0.6-0.7	47
0.7-0.8	2
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
0.7526	Intermediate Similarity	NPD46	Approved
0.7526	Intermediate Similarity	NPD6698	Approved
0.7358	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7838	Discovery
0.729	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7328	Approved
0.687	Remote Similarity	NPD7327	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6847	Remote Similarity	NPD6371	Approved
0.6838	Remote Similarity	NPD8033	Approved
0.681	Remote Similarity	NPD7516	Approved
0.6765	Remote Similarity	NPD7983	Approved
0.6752	Remote Similarity	NPD8377	Approved
0.6752	Remote Similarity	NPD8294	Approved
0.6729	Remote Similarity	NPD5344	Discontinued
0.6721	Remote Similarity	NPD7319	Approved
0.6695	Remote Similarity	NPD8515	Approved
0.6695	Remote Similarity	NPD8516	Approved
0.6695	Remote Similarity	NPD8517	Approved
0.6695	Remote Similarity	NPD8380	Approved
0.6695	Remote Similarity	NPD8296	Approved
0.6695	Remote Similarity	NPD8379	Approved
0.6695	Remote Similarity	NPD8335	Approved
0.6695	Remote Similarity	NPD8378	Approved
0.6695	Remote Similarity	NPD8513	Phase 3
0.6612	Remote Similarity	NPD7507	Approved
0.6607	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8080	Discontinued
0.6496	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5282	Discontinued
0.6446	Remote Similarity	NPD7642	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.6423	Remote Similarity	NPD8074	Phase 3
0.6417	Remote Similarity	NPD7503	Approved
0.6404	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7839	Suspended
0.633	Remote Similarity	NPD6648	Approved
0.6311	Remote Similarity	NPD7829	Approved
0.6311	Remote Similarity	NPD7830	Approved
0.6281	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD1695	Approved
0.6231	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD4250	Approved
0.621	Remote Similarity	NPD8451	Approved
0.6176	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8448	Approved
0.6148	Remote Similarity	NPD8269	Approved
0.6148	Remote Similarity	NPD8267	Approved
0.6148	Remote Similarity	NPD8444	Approved
0.6148	Remote Similarity	NPD8268	Approved
0.6148	Remote Similarity	NPD8266	Approved
0.614	Remote Similarity	NPD6412	Phase 2
0.614	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD8133	Approved
0.6091	Remote Similarity	NPD7638	Approved
0.6083	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7505	Discontinued
0.608	Remote Similarity	NPD8273	Phase 1
0.6075	Remote Similarity	NPD5779	Approved
0.6075	Remote Similarity	NPD5778	Approved
0.6044	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD7639	Approved
0.6034	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8392	Approved
0.6016	Remote Similarity	NPD8390	Approved
0.6016	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD8340	Approved
0.5981	Remote Similarity	NPD7637	Suspended
0.5952	Remote Similarity	NPD6616	Approved
0.595	Remote Similarity	NPD7115	Discovery
0.5935	Remote Similarity	NPD6059	Approved
0.5935	Remote Similarity	NPD6054	Approved
0.5929	Remote Similarity	NPD7632	Discontinued
0.592	Remote Similarity	NPD8328	Phase 3
0.5906	Remote Similarity	NPD8293	Discontinued
0.5906	Remote Similarity	NPD7078	Approved
0.5902	Remote Similarity	NPD7641	Discontinued
0.5895	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5785	Approved
0.5887	Remote Similarity	NPD6015	Approved
0.5887	Remote Similarity	NPD6016	Approved
0.5859	Remote Similarity	NPD7736	Approved
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	Approved
0.5842	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4822	Approved
0.584	Remote Similarity	NPD6370	Approved
0.584	Remote Similarity	NPD5988	Approved
0.5825	Remote Similarity	NPD7154	Phase 3
0.5825	Remote Similarity	NPD3669	Approved
0.5825	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6319	Approved
0.5798	Remote Similarity	NPD2204	Approved
0.5794	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6101	Approved
0.5776	Remote Similarity	NPD4211	Phase 1
0.5755	Remote Similarity	NPD7524	Approved
0.573	Remote Similarity	NPD69	Approved
0.573	Remote Similarity	NPD9119	Approved
0.5728	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5363	Approved
0.5691	Remote Similarity	NPD7500	Approved
0.5688	Remote Similarity	NPD6411	Approved
0.5673	Remote Similarity	NPD5362	Discontinued
0.5644	Remote Similarity	NPD4268	Approved
0.5644	Remote Similarity	NPD4271	Approved
0.5631	Remote Similarity	NPD5369	Approved
0.562	Remote Similarity	NPD969	Suspended
0.5619	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD9118	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