NPASS Compound

Structure

NPC473333 OpenBabel07101719152D 23 25 0 0 1 0 0 0 0 0999 V2000 0.1019 1.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0659 -1.9835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9062 -1.8768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 -1.3143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3239 -1.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7361 -0.3633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9271 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9271 0.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1180 -0.3633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9271 0.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 -1.3143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7361 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8781 0.5335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.2925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5877 -1.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3184 -1.0678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 0.5878 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 2 15 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 1 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 1 1 6 0 0 0 14 23 1 0 0 0 0 15 16 1 6 0 0 0 15 19 1 0 0 0 0 16 20 1 6 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.14
Volume:	313.245
LogP:	1.184
LogD:	1.372
LogS:	-2.477
# Rotatable Bonds:	2
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	5.819
Fsp3:	0.688
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:	-5.376
MDCK Permeability:	9.413457519258372e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.688
Plasma Protein Binding (PPB):	60.77186584472656%
Volume Distribution (VD):	1.73
Pgp-substrate:	32.07819747924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.546
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.117
CYP3A4-substrate:	0.497

ADMET: Excretion

Clearance (CL):	10.311
Half-life (T1/2):	0.377

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.516
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.282
Carcinogencity:	0.986
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC473333

Natural Product ID:	NPC473333
*Common Name:**	Spicatolides D
IUPAC Name:	n.a.
Synonyms:	spicatolides D
Standard InCHIKey:	KSBUVUDANITIFW-AREORGLZSA-N
Standard InCHI:	InChI=1S/C16H22O7/c1-14-4-5-16(20,23-14)15(2,19)6-10(17)12-9(8-21-3)13(18)22-11(12)7-14/h7,10,17,19-20H,4-6,8H2,1-3H3/b11-7+/t10-,14+,15-,16-/m0/s1
SMILES:	COCC1=C2/C(=C[C@@]3(C)CC[C@@]([C@@](C[C@@H]2O)(C)O)(O3)O)/OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401284
PubChem CID:	44445359
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5.1	ug.mL-1	PMID[488752]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[488752]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[488752]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[488752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.8	ug.mL-1	PMID[488752]

☑ 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 NPC473333 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	204
0.1-0.2	1290
0.2-0.3	4540
0.3-0.4	8736
0.4-0.5	16854
0.5-0.6	7571
0.6-0.7	2999
0.7-0.8	470
0.8-0.85	13
0.85-0.9	9
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC2666
0.9667	High Similarity	NPC471492
0.9457	High Similarity	NPC471490
0.9222	High Similarity	NPC3436
0.9121	High Similarity	NPC470520
0.9111	High Similarity	NPC225283
0.9022	High Similarity	NPC59646
0.8925	High Similarity	NPC470521
0.871	High Similarity	NPC32494
0.871	High Similarity	NPC175842
0.8421	Intermediate Similarity	NPC471483
0.8367	Intermediate Similarity	NPC187268
0.835	Intermediate Similarity	NPC38154
0.8298	Intermediate Similarity	NPC64913
0.8298	Intermediate Similarity	NPC242877
0.8119	Intermediate Similarity	NPC303653
0.8119	Intermediate Similarity	NPC189609
0.8119	Intermediate Similarity	NPC140591
0.8119	Intermediate Similarity	NPC197835
0.8119	Intermediate Similarity	NPC291500
0.8081	Intermediate Similarity	NPC471462
0.8	Intermediate Similarity	NPC260343
0.7959	Intermediate Similarity	NPC474338
0.7938	Intermediate Similarity	NPC158061
0.7789	Intermediate Similarity	NPC311163
0.77	Intermediate Similarity	NPC220221
0.7684	Intermediate Similarity	NPC471494
0.7677	Intermediate Similarity	NPC272293
0.7677	Intermediate Similarity	NPC32862
0.7677	Intermediate Similarity	NPC40821
0.7677	Intermediate Similarity	NPC475912
0.7647	Intermediate Similarity	NPC203627
0.7624	Intermediate Similarity	NPC98165
0.7624	Intermediate Similarity	NPC299396
0.7624	Intermediate Similarity	NPC301596
0.7624	Intermediate Similarity	NPC288350
0.7624	Intermediate Similarity	NPC173329
0.7619	Intermediate Similarity	NPC100487
0.7604	Intermediate Similarity	NPC61527
0.76	Intermediate Similarity	NPC256368
0.7579	Intermediate Similarity	NPC475706
0.7576	Intermediate Similarity	NPC114345
0.7576	Intermediate Similarity	NPC327760
0.7576	Intermediate Similarity	NPC6099
0.7576	Intermediate Similarity	NPC303230
0.7573	Intermediate Similarity	NPC288876
0.7551	Intermediate Similarity	NPC473564
0.7551	Intermediate Similarity	NPC133450
0.7549	Intermediate Similarity	NPC218064
0.7525	Intermediate Similarity	NPC36954
0.7525	Intermediate Similarity	NPC14961
0.7525	Intermediate Similarity	NPC270013
0.75	Intermediate Similarity	NPC81419
0.75	Intermediate Similarity	NPC4637
0.75	Intermediate Similarity	NPC238090
0.75	Intermediate Similarity	NPC179746
0.75	Intermediate Similarity	NPC472195
0.75	Intermediate Similarity	NPC472196
0.75	Intermediate Similarity	NPC219038
0.75	Intermediate Similarity	NPC475098
0.75	Intermediate Similarity	NPC189651
0.75	Intermediate Similarity	NPC20673
0.75	Intermediate Similarity	NPC11804
0.75	Intermediate Similarity	NPC98859
0.7476	Intermediate Similarity	NPC473326
0.7475	Intermediate Similarity	NPC177668
0.7475	Intermediate Similarity	NPC118078
0.7475	Intermediate Similarity	NPC474761
0.7475	Intermediate Similarity	NPC206614
0.7475	Intermediate Similarity	NPC473448
0.7475	Intermediate Similarity	NPC473904
0.7475	Intermediate Similarity	NPC474323
0.7475	Intermediate Similarity	NPC476004
0.7451	Intermediate Similarity	NPC230800
0.7451	Intermediate Similarity	NPC279621
0.7451	Intermediate Similarity	NPC172998
0.7447	Intermediate Similarity	NPC474894
0.7431	Intermediate Similarity	NPC235014
0.7429	Intermediate Similarity	NPC471599
0.7429	Intermediate Similarity	NPC86077
0.7426	Intermediate Similarity	NPC159698
0.7426	Intermediate Similarity	NPC81386
0.7426	Intermediate Similarity	NPC474035
0.7423	Intermediate Similarity	NPC204048
0.7407	Intermediate Similarity	NPC473807
0.7407	Intermediate Similarity	NPC38948
0.7404	Intermediate Similarity	NPC244878
0.7404	Intermediate Similarity	NPC475053
0.74	Intermediate Similarity	NPC30515
0.74	Intermediate Similarity	NPC12172
0.74	Intermediate Similarity	NPC184463
0.74	Intermediate Similarity	NPC208886
0.7396	Intermediate Similarity	NPC186155
0.7396	Intermediate Similarity	NPC78673
0.7396	Intermediate Similarity	NPC160517
0.7383	Intermediate Similarity	NPC239961
0.7379	Intermediate Similarity	NPC266842
0.7374	Intermediate Similarity	NPC139418
0.7374	Intermediate Similarity	NPC295312
0.7368	Intermediate Similarity	NPC474959
0.7368	Intermediate Similarity	NPC310450
0.7368	Intermediate Similarity	NPC11383
0.7368	Intermediate Similarity	NPC475046
0.7358	Intermediate Similarity	NPC472755
0.7358	Intermediate Similarity	NPC475945
0.7358	Intermediate Similarity	NPC475871
0.7353	Intermediate Similarity	NPC471142
0.7353	Intermediate Similarity	NPC107476
0.7353	Intermediate Similarity	NPC272050
0.7353	Intermediate Similarity	NPC471141
0.7353	Intermediate Similarity	NPC304886
0.7353	Intermediate Similarity	NPC234339
0.7353	Intermediate Similarity	NPC273197
0.7347	Intermediate Similarity	NPC475037
0.7347	Intermediate Similarity	NPC191283
0.7347	Intermediate Similarity	NPC160138
0.7339	Intermediate Similarity	NPC206618
0.7333	Intermediate Similarity	NPC474339
0.7333	Intermediate Similarity	NPC128733
0.7333	Intermediate Similarity	NPC185141
0.7333	Intermediate Similarity	NPC472753
0.7333	Intermediate Similarity	NPC46998
0.7333	Intermediate Similarity	NPC133907
0.7333	Intermediate Similarity	NPC473332
0.7333	Intermediate Similarity	NPC110443
0.7333	Intermediate Similarity	NPC150923
0.7333	Intermediate Similarity	NPC164598
0.7328	Intermediate Similarity	NPC287236
0.7327	Intermediate Similarity	NPC475838
0.7327	Intermediate Similarity	NPC476300
0.7327	Intermediate Similarity	NPC228451
0.7327	Intermediate Similarity	NPC469692
0.7327	Intermediate Similarity	NPC125674
0.7327	Intermediate Similarity	NPC469645
0.7327	Intermediate Similarity	NPC156553
0.7327	Intermediate Similarity	NPC212486
0.7321	Intermediate Similarity	NPC106446
0.732	Intermediate Similarity	NPC120398
0.732	Intermediate Similarity	NPC475034
0.732	Intermediate Similarity	NPC471567
0.732	Intermediate Similarity	NPC471185
0.732	Intermediate Similarity	NPC67081
0.732	Intermediate Similarity	NPC471223
0.7315	Intermediate Similarity	NPC474285
0.7315	Intermediate Similarity	NPC254538
0.7315	Intermediate Similarity	NPC475074
0.7312	Intermediate Similarity	NPC3852
0.7308	Intermediate Similarity	NPC151093
0.7308	Intermediate Similarity	NPC475068
0.7308	Intermediate Similarity	NPC471144
0.73	Intermediate Similarity	NPC3952
0.73	Intermediate Similarity	NPC80875
0.73	Intermediate Similarity	NPC475855
0.73	Intermediate Similarity	NPC474232
0.73	Intermediate Similarity	NPC51004
0.7297	Intermediate Similarity	NPC66108
0.7292	Intermediate Similarity	NPC229799
0.7292	Intermediate Similarity	NPC231601
0.7292	Intermediate Similarity	NPC475714
0.7292	Intermediate Similarity	NPC161045
0.7292	Intermediate Similarity	NPC286770
0.7292	Intermediate Similarity	NPC284472
0.729	Intermediate Similarity	NPC474917
0.729	Intermediate Similarity	NPC161775
0.729	Intermediate Similarity	NPC146731
0.729	Intermediate Similarity	NPC203659
0.729	Intermediate Similarity	NPC296950
0.7282	Intermediate Similarity	NPC476315
0.7282	Intermediate Similarity	NPC477921
0.7282	Intermediate Similarity	NPC472995
0.7282	Intermediate Similarity	NPC473859
0.7273	Intermediate Similarity	NPC233551
0.7273	Intermediate Similarity	NPC48338
0.7273	Intermediate Similarity	NPC40376
0.7273	Intermediate Similarity	NPC21208
0.7273	Intermediate Similarity	NPC202672
0.7273	Intermediate Similarity	NPC280621
0.7273	Intermediate Similarity	NPC20339
0.7264	Intermediate Similarity	NPC474747
0.7264	Intermediate Similarity	NPC471148
0.7264	Intermediate Similarity	NPC472754
0.7264	Intermediate Similarity	NPC472815
0.7264	Intermediate Similarity	NPC149371
0.7255	Intermediate Similarity	NPC472198
0.7255	Intermediate Similarity	NPC121825
0.7255	Intermediate Similarity	NPC474247
0.7248	Intermediate Similarity	NPC50124
0.7248	Intermediate Similarity	NPC475960
0.7245	Intermediate Similarity	NPC114694
0.7245	Intermediate Similarity	NPC240695
0.7245	Intermediate Similarity	NPC107717
0.7245	Intermediate Similarity	NPC231096
0.7245	Intermediate Similarity	NPC232555
0.7245	Intermediate Similarity	NPC62118
0.7245	Intermediate Similarity	NPC171174
0.7245	Intermediate Similarity	NPC475581
0.7245	Intermediate Similarity	NPC142117
0.7238	Intermediate Similarity	NPC469864
0.7238	Intermediate Similarity	NPC469872
0.7238	Intermediate Similarity	NPC272223

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 NPC473333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1732
0.2-0.3	3752
0.3-0.4	2410
0.4-0.5	821
0.5-0.6	193
0.6-0.7	50
0.7-0.8	3
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
0.7653	Intermediate Similarity	NPD7838	Discovery
0.7308	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7983	Approved
0.7156	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD46	Approved
0.7129	Intermediate Similarity	NPD6698	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6964	Remote Similarity	NPD6371	Approved
0.69	Remote Similarity	NPD4249	Approved
0.6852	Remote Similarity	NPD5344	Discontinued
0.6832	Remote Similarity	NPD4251	Approved
0.6832	Remote Similarity	NPD4250	Approved
0.6786	Remote Similarity	NPD6686	Approved
0.6759	Remote Similarity	NPD6648	Approved
0.6754	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6604	Remote Similarity	NPD5282	Discontinued
0.6542	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7503	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD7839	Suspended
0.6436	Remote Similarity	NPD7154	Phase 3
0.6417	Remote Similarity	NPD7328	Approved
0.6417	Remote Similarity	NPD7327	Approved
0.6415	Remote Similarity	NPD7637	Suspended
0.641	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD8074	Phase 3
0.6393	Remote Similarity	NPD8033	Approved
0.6364	Remote Similarity	NPD7516	Approved
0.6311	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8377	Approved
0.6299	Remote Similarity	NPD7319	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8335	Approved
0.626	Remote Similarity	NPD8296	Approved
0.626	Remote Similarity	NPD8380	Approved
0.626	Remote Similarity	NPD8378	Approved
0.626	Remote Similarity	NPD8379	Approved
0.6226	Remote Similarity	NPD1695	Approved
0.6198	Remote Similarity	NPD7505	Discontinued
0.6196	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7524	Approved
0.619	Remote Similarity	NPD7507	Approved
0.6168	Remote Similarity	NPD5785	Approved
0.6161	Remote Similarity	NPD7640	Approved
0.6161	Remote Similarity	NPD7639	Approved
0.616	Remote Similarity	NPD7829	Approved
0.616	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8080	Discontinued
0.6071	Remote Similarity	NPD7638	Approved
0.6066	Remote Similarity	NPD7115	Discovery
0.6066	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8273	Phase 1
0.6063	Remote Similarity	NPD8451	Approved
0.6058	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7642	Approved
0.6019	Remote Similarity	NPD5209	Approved
0.6016	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD5363	Approved
0.5984	Remote Similarity	NPD8341	Approved
0.5984	Remote Similarity	NPD8340	Approved
0.5984	Remote Similarity	NPD8299	Approved
0.5984	Remote Similarity	NPD8342	Approved
0.5966	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6110	Phase 1
0.5962	Remote Similarity	NPD6695	Phase 3
0.5962	Remote Similarity	NPD5362	Discontinued
0.5941	Remote Similarity	NPD4268	Approved
0.5941	Remote Similarity	NPD4271	Approved
0.5935	Remote Similarity	NPD7500	Approved
0.5926	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6101	Approved
0.5917	Remote Similarity	NPD2204	Approved
0.5878	Remote Similarity	NPD8391	Approved
0.5878	Remote Similarity	NPD8392	Approved
0.5878	Remote Similarity	NPD8390	Approved
0.5873	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD969	Suspended
0.5865	Remote Similarity	NPD4269	Approved
0.5865	Remote Similarity	NPD4270	Approved
0.5859	Remote Similarity	NPD7492	Approved
0.5847	Remote Similarity	NPD6412	Phase 2
0.5842	Remote Similarity	NPD4756	Discovery
0.5818	Remote Similarity	NPD6411	Approved
0.5814	Remote Similarity	NPD6616	Approved
0.581	Remote Similarity	NPD5331	Approved
0.581	Remote Similarity	NPD5332	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5794	Remote Similarity	NPD5786	Approved
0.5794	Remote Similarity	NPD6054	Approved
0.5776	Remote Similarity	NPD7632	Discontinued
0.5769	Remote Similarity	NPD4790	Discontinued
0.5769	Remote Similarity	NPD8293	Discontinued
0.5769	Remote Similarity	NPD5369	Approved
0.5769	Remote Similarity	NPD7078	Approved
0.576	Remote Similarity	NPD7641	Discontinued
0.5748	Remote Similarity	NPD6016	Approved
0.5748	Remote Similarity	NPD6015	Approved
0.5741	Remote Similarity	NPD7750	Discontinued
0.5725	Remote Similarity	NPD7736	Approved
0.5714	Remote Similarity	NPD9119	Approved
0.5714	Remote Similarity	NPD69	Approved
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD5988	Approved
0.5703	Remote Similarity	NPD6370	Approved
0.5702	Remote Similarity	NPD2067	Discontinued
0.5673	Remote Similarity	NPD6930	Phase 2
0.5673	Remote Similarity	NPD4252	Approved
0.5673	Remote Similarity	NPD6931	Approved
0.5669	Remote Similarity	NPD6319	Approved
0.5667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD694	Clinical (unspecified phase)
0.563	Remote Similarity	NPD4211	Phase 1
0.5614	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5604	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