NPASS Compound

Structure

NPC471496 OpenBabel07101719522D 28 30 0 0 1 0 0 0 0 0999 V2000 -4.3914 4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8164 2.7509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4031 -0.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 1.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9848 1.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 1.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7441 4.6622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 1.3473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5825 2.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 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 10 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 25 1 0 0 0 0 9 17 1 0 0 0 0 10 20 2 0 0 0 0 10 25 1 0 0 0 0 11 21 2 0 0 0 0 11 26 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 1 0 0 0 14 18 1 0 0 0 0 14 22 2 0 0 0 0 15 19 1 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 3 1 1 0 0 0 17 24 1 0 0 0 0 18 4 1 1 0 0 0 18 28 1 0 0 0 0 19 9 1 1 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.14
Volume:	377.441
LogP:	1.085
LogD:	1.038
LogS:	-2.758
# Rotatable Bonds:	5
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	5.902
Fsp3:	0.684
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:	-5.118
MDCK Permeability:	5.660742681357078e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.137
Human Intestinal Absorption (HIA):	0.102
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	44.00619888305664%
Volume Distribution (VD):	0.644
Pgp-substrate:	59.11246109008789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.449
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.391
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	3.96
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.901
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.749
Skin Sensitization:	0.617
Carcinogencity:	0.75
Eye Corrosion:	0.052
Eye Irritation:	0.069
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC471496

Natural Product ID:	NPC471496
*Common Name:**	Spicatolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CIQHYIPVUYZISN-CJODITQLSA-N
Standard InCHI:	InChI=1S/C19H24O9/c1-10(20)25-8-12-15-13(26-11(2)21)7-18(4)14(22)5-6-17(3,24)9-19(15,28-18)27-16(12)23/h13,24H,5-9H2,1-4H3/t13-,17+,18+,19-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@]2(C)O[C@]3(C1=C(COC(=O)C)C(=O)O3)C[C@](CCC2=O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253117
PubChem CID:	44445367
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
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	3

Activity Type	# Activity
Cell Line	3

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[548997]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[548997]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[548997]

☑ 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 NPC471496 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	225
0.1-0.2	1658
0.2-0.3	5659
0.3-0.4	10354
0.4-0.5	14229
0.5-0.6	7477
0.6-0.7	2973
0.7-0.8	120
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9663	High Similarity	NPC473334
0.81	Intermediate Similarity	NPC313569
0.7835	Intermediate Similarity	NPC471483
0.77	Intermediate Similarity	NPC471462
0.77	Intermediate Similarity	NPC218064
0.7647	Intermediate Similarity	NPC164598
0.7647	Intermediate Similarity	NPC474339
0.7596	Intermediate Similarity	NPC472748
0.7579	Intermediate Similarity	NPC261721
0.7576	Intermediate Similarity	NPC469632
0.7573	Intermediate Similarity	NPC149371
0.7525	Intermediate Similarity	NPC266842
0.7524	Intermediate Similarity	NPC472749
0.7524	Intermediate Similarity	NPC472751
0.75	Intermediate Similarity	NPC472750
0.75	Intermediate Similarity	NPC227494
0.75	Intermediate Similarity	NPC472747
0.75	Intermediate Similarity	NPC197333
0.7476	Intermediate Similarity	NPC474742
0.7476	Intermediate Similarity	NPC47880
0.7429	Intermediate Similarity	NPC472756
0.7426	Intermediate Similarity	NPC230800
0.7423	Intermediate Similarity	NPC469628
0.7423	Intermediate Similarity	NPC471047
0.7423	Intermediate Similarity	NPC475906
0.7423	Intermediate Similarity	NPC469631
0.7423	Intermediate Similarity	NPC469653
0.7407	Intermediate Similarity	NPC89408
0.7404	Intermediate Similarity	NPC189609
0.7404	Intermediate Similarity	NPC303653
0.7404	Intermediate Similarity	NPC291500
0.7404	Intermediate Similarity	NPC472754
0.7404	Intermediate Similarity	NPC197835
0.7404	Intermediate Similarity	NPC140591
0.74	Intermediate Similarity	NPC121825
0.74	Intermediate Similarity	NPC474338
0.7396	Intermediate Similarity	NPC469483
0.7396	Intermediate Similarity	NPC279859
0.7396	Intermediate Similarity	NPC38576
0.7374	Intermediate Similarity	NPC20713
0.7353	Intermediate Similarity	NPC40812
0.7347	Intermediate Similarity	NPC205548
0.7333	Intermediate Similarity	NPC475945
0.7333	Intermediate Similarity	NPC475871
0.7333	Intermediate Similarity	NPC472755
0.7327	Intermediate Similarity	NPC471141
0.732	Intermediate Similarity	NPC160138
0.7315	Intermediate Similarity	NPC38154
0.7308	Intermediate Similarity	NPC472753
0.7308	Intermediate Similarity	NPC201718
0.7303	Intermediate Similarity	NPC144419
0.73	Intermediate Similarity	NPC320089
0.73	Intermediate Similarity	NPC469645
0.73	Intermediate Similarity	NPC469692
0.7292	Intermediate Similarity	NPC473353
0.729	Intermediate Similarity	NPC477513
0.7282	Intermediate Similarity	NPC261377
0.7282	Intermediate Similarity	NPC472015
0.7282	Intermediate Similarity	NPC471144
0.7282	Intermediate Similarity	NPC255592
0.7282	Intermediate Similarity	NPC308567
0.7273	Intermediate Similarity	NPC144133
0.7273	Intermediate Similarity	NPC179394
0.7273	Intermediate Similarity	NPC471569
0.7264	Intermediate Similarity	NPC474917
0.7264	Intermediate Similarity	NPC474741
0.7255	Intermediate Similarity	NPC143446
0.7255	Intermediate Similarity	NPC299396
0.7255	Intermediate Similarity	NPC172998
0.7255	Intermediate Similarity	NPC301596
0.7255	Intermediate Similarity	NPC240673
0.7255	Intermediate Similarity	NPC17578
0.7245	Intermediate Similarity	NPC475902
0.7241	Intermediate Similarity	NPC186339
0.7238	Intermediate Similarity	NPC471148
0.7238	Intermediate Similarity	NPC474747
0.7228	Intermediate Similarity	NPC474247
0.7222	Intermediate Similarity	NPC475960
0.7222	Intermediate Similarity	NPC322903
0.7212	Intermediate Similarity	NPC54705
0.7212	Intermediate Similarity	NPC280963
0.72	Intermediate Similarity	NPC470379
0.72	Intermediate Similarity	NPC470373
0.72	Intermediate Similarity	NPC472705
0.7196	Intermediate Similarity	NPC475802
0.7196	Intermediate Similarity	NPC16313
0.7196	Intermediate Similarity	NPC472645
0.7196	Intermediate Similarity	NPC9303
0.7184	Intermediate Similarity	NPC471140
0.7172	Intermediate Similarity	NPC475971
0.7172	Intermediate Similarity	NPC32922
0.7172	Intermediate Similarity	NPC295312
0.717	Intermediate Similarity	NPC320154
0.717	Intermediate Similarity	NPC4620
0.717	Intermediate Similarity	NPC475873
0.7157	Intermediate Similarity	NPC273197
0.7157	Intermediate Similarity	NPC471492
0.7157	Intermediate Similarity	NPC234339
0.7143	Intermediate Similarity	NPC185141
0.7143	Intermediate Similarity	NPC472007
0.7143	Intermediate Similarity	NPC476270
0.7143	Intermediate Similarity	NPC133907
0.7143	Intermediate Similarity	NPC477511
0.7143	Intermediate Similarity	NPC473332
0.7143	Intermediate Similarity	NPC72513
0.7143	Intermediate Similarity	NPC46998
0.7143	Intermediate Similarity	NPC264477
0.7143	Intermediate Similarity	NPC15993
0.7143	Intermediate Similarity	NPC128733
0.7143	Intermediate Similarity	NPC110443
0.713	Intermediate Similarity	NPC26617
0.713	Intermediate Similarity	NPC194620
0.713	Intermediate Similarity	NPC72813
0.713	Intermediate Similarity	NPC163693
0.713	Intermediate Similarity	NPC147635
0.713	Intermediate Similarity	NPC326994
0.713	Intermediate Similarity	NPC474421
0.713	Intermediate Similarity	NPC324327
0.7129	Intermediate Similarity	NPC228451
0.7129	Intermediate Similarity	NPC125674
0.7129	Intermediate Similarity	NPC475302
0.7129	Intermediate Similarity	NPC476300
0.7129	Intermediate Similarity	NPC475838
0.7117	Intermediate Similarity	NPC66108
0.7117	Intermediate Similarity	NPC317687
0.7115	Intermediate Similarity	NPC83895
0.7115	Intermediate Similarity	NPC187268
0.7115	Intermediate Similarity	NPC187761
0.7113	Intermediate Similarity	NPC67081
0.7113	Intermediate Similarity	NPC471223
0.7113	Intermediate Similarity	NPC92633
0.7113	Intermediate Similarity	NPC261380
0.7113	Intermediate Similarity	NPC215364
0.7103	Intermediate Similarity	NPC220964
0.7103	Intermediate Similarity	NPC475676
0.71	Intermediate Similarity	NPC106510
0.71	Intermediate Similarity	NPC475855
0.71	Intermediate Similarity	NPC473448
0.71	Intermediate Similarity	NPC71533
0.7091	Intermediate Similarity	NPC476766
0.7091	Intermediate Similarity	NPC472666
0.7087	Intermediate Similarity	NPC76862
0.7087	Intermediate Similarity	NPC476275
0.7087	Intermediate Similarity	NPC158416
0.7087	Intermediate Similarity	NPC306041
0.7087	Intermediate Similarity	NPC470883
0.7087	Intermediate Similarity	NPC17585
0.7087	Intermediate Similarity	NPC476009
0.7087	Intermediate Similarity	NPC39859
0.7087	Intermediate Similarity	NPC54731
0.7087	Intermediate Similarity	NPC279621
0.7083	Intermediate Similarity	NPC128429
0.7083	Intermediate Similarity	NPC250315
0.7083	Intermediate Similarity	NPC318468
0.7083	Intermediate Similarity	NPC69469
0.7075	Intermediate Similarity	NPC39996
0.7075	Intermediate Similarity	NPC320019
0.7075	Intermediate Similarity	NPC324017
0.7064	Intermediate Similarity	NPC327286
0.7064	Intermediate Similarity	NPC219900
0.7064	Intermediate Similarity	NPC169888
0.7064	Intermediate Similarity	NPC233379
0.7064	Intermediate Similarity	NPC55972
0.7064	Intermediate Similarity	NPC177524
0.7064	Intermediate Similarity	NPC392
0.7064	Intermediate Similarity	NPC474664
0.7064	Intermediate Similarity	NPC14862
0.7059	Intermediate Similarity	NPC475832
0.7059	Intermediate Similarity	NPC71589
0.7059	Intermediate Similarity	NPC476267
0.7059	Intermediate Similarity	NPC140543
0.7059	Intermediate Similarity	NPC477131
0.7059	Intermediate Similarity	NPC475927
0.7059	Intermediate Similarity	NPC474555
0.7059	Intermediate Similarity	NPC190294
0.7059	Intermediate Similarity	NPC474554
0.7059	Intermediate Similarity	NPC11732
0.7048	Intermediate Similarity	NPC469551
0.7048	Intermediate Similarity	NPC475949
0.7048	Intermediate Similarity	NPC288876
0.7041	Intermediate Similarity	NPC472009
0.7041	Intermediate Similarity	NPC162071
0.7041	Intermediate Similarity	NPC284902
0.703	Intermediate Similarity	NPC261607
0.703	Intermediate Similarity	NPC141831
0.703	Intermediate Similarity	NPC329952
0.703	Intermediate Similarity	NPC300312
0.703	Intermediate Similarity	NPC473707
0.703	Intermediate Similarity	NPC111114
0.703	Intermediate Similarity	NPC158061
0.7027	Intermediate Similarity	NPC126897
0.7027	Intermediate Similarity	NPC297945
0.7027	Intermediate Similarity	NPC317107
0.7021	Intermediate Similarity	NPC276647
0.7021	Intermediate Similarity	NPC622
0.7019	Intermediate Similarity	NPC2666
0.7019	Intermediate Similarity	NPC108475
0.7019	Intermediate Similarity	NPC213947
0.7019	Intermediate Similarity	NPC471490
0.7019	Intermediate Similarity	NPC170143

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 NPC471496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2231
0.2-0.3	3784
0.3-0.4	1953
0.4-0.5	661
0.5-0.6	281
0.6-0.7	34
0.7-0.8	0
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
0.713	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD46	Approved
0.71	Intermediate Similarity	NPD6698	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.7027	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8080	Discontinued
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6371	Approved
0.6604	Remote Similarity	NPD7839	Suspended
0.6509	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5785	Approved
0.6434	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7319	Approved
0.6393	Remote Similarity	NPD8328	Phase 3
0.6393	Remote Similarity	NPD7642	Approved
0.6381	Remote Similarity	NPD7983	Approved
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.6355	Remote Similarity	NPD5695	Phase 3
0.633	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD5778	Approved
0.6321	Remote Similarity	NPD5779	Approved
0.6303	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7507	Approved
0.6286	Remote Similarity	NPD7838	Discovery
0.6275	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5363	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6239	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD6083	Phase 2
0.6224	Remote Similarity	NPD4238	Approved
0.6224	Remote Similarity	NPD4802	Phase 2
0.621	Remote Similarity	NPD7492	Approved
0.62	Remote Similarity	NPD5369	Approved
0.619	Remote Similarity	NPD1695	Approved
0.6182	Remote Similarity	NPD4225	Approved
0.6182	Remote Similarity	NPD7638	Approved
0.6176	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6616	Approved
0.6148	Remote Similarity	NPD6054	Approved
0.6148	Remote Similarity	NPD6319	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6139	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD4269	Approved
0.6126	Remote Similarity	NPD7640	Approved
0.6126	Remote Similarity	NPD7639	Approved
0.6122	Remote Similarity	NPD4756	Discovery
0.6121	Remote Similarity	NPD6373	Approved
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD8293	Discontinued
0.6111	Remote Similarity	NPD7078	Approved
0.6102	Remote Similarity	NPD6053	Discontinued
0.6098	Remote Similarity	NPD6016	Approved
0.6098	Remote Similarity	NPD6015	Approved
0.6087	Remote Similarity	NPD6412	Phase 2
0.6087	Remote Similarity	NPD3704	Approved
0.6078	Remote Similarity	NPD7154	Phase 3
0.6075	Remote Similarity	NPD5693	Phase 1
0.6063	Remote Similarity	NPD7736	Approved
0.6058	Remote Similarity	NPD5786	Approved
0.6048	Remote Similarity	NPD6370	Approved
0.6048	Remote Similarity	NPD5988	Approved
0.6038	Remote Similarity	NPD6101	Approved
0.6038	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7115	Discovery
0.6033	Remote Similarity	NPD6009	Approved
0.6032	Remote Similarity	NPD8451	Approved
0.6018	Remote Similarity	NPD7632	Discontinued
0.6017	Remote Similarity	NPD6650	Approved
0.6017	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD7830	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD8448	Approved
0.5984	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD7327	Approved
0.598	Remote Similarity	NPD5209	Approved
0.5978	Remote Similarity	NPD7341	Phase 2
0.5978	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8444	Approved
0.5948	Remote Similarity	NPD5701	Approved
0.5948	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6672	Approved
0.5943	Remote Similarity	NPD5737	Approved
0.5941	Remote Similarity	NPD4252	Approved
0.5935	Remote Similarity	NPD7516	Approved
0.5926	Remote Similarity	NPD6411	Approved
0.5922	Remote Similarity	NPD6110	Phase 1
0.5917	Remote Similarity	NPD8133	Approved
0.5897	Remote Similarity	NPD7320	Approved
0.5897	Remote Similarity	NPD6899	Approved
0.5897	Remote Similarity	NPD6881	Approved
0.5887	Remote Similarity	NPD8294	Approved
0.5887	Remote Similarity	NPD8377	Approved
0.5865	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7641	Discontinued
0.5847	Remote Similarity	NPD6013	Approved
0.5847	Remote Similarity	NPD6014	Approved
0.5847	Remote Similarity	NPD6012	Approved
0.5846	Remote Similarity	NPD8391	Approved
0.5846	Remote Similarity	NPD8390	Approved
0.5846	Remote Similarity	NPD8392	Approved
0.584	Remote Similarity	NPD8380	Approved
0.584	Remote Similarity	NPD8378	Approved
0.584	Remote Similarity	NPD8335	Approved
0.584	Remote Similarity	NPD8379	Approved
0.584	Remote Similarity	NPD8296	Approved
0.584	Remote Similarity	NPD8033	Approved
0.5833	Remote Similarity	NPD8297	Approved
0.5827	Remote Similarity	NPD8340	Approved
0.5827	Remote Similarity	NPD8341	Approved
0.5827	Remote Similarity	NPD8342	Approved
0.5827	Remote Similarity	NPD8299	Approved
0.5825	Remote Similarity	NPD6435	Approved
0.581	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7260	Phase 2
0.5798	Remote Similarity	NPD7290	Approved
0.5798	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD7102	Approved
0.5789	Remote Similarity	NPD8415	Approved
0.5789	Remote Similarity	NPD5344	Discontinued
0.578	Remote Similarity	NPD7637	Suspended
0.5772	Remote Similarity	NPD7500	Approved
0.5769	Remote Similarity	NPD5362	Discontinued
0.5763	Remote Similarity	NPD6011	Approved
0.5758	Remote Similarity	NPD8039	Approved
0.5758	Remote Similarity	NPD6845	Suspended
0.5755	Remote Similarity	NPD4249	Approved
0.575	Remote Similarity	NPD6869	Approved
0.575	Remote Similarity	NPD8130	Phase 1
0.575	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD6617	Approved
0.5745	Remote Similarity	NPD7331	Phase 2
0.5743	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6080	Approved
0.5741	Remote Similarity	NPD6673	Approved
0.5741	Remote Similarity	NPD6904	Approved
0.5741	Remote Similarity	NPD4753	Phase 2
0.5727	Remote Similarity	NPD6399	Phase 3
0.5726	Remote Similarity	NPD4211	Phase 1
0.5725	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD6921	Approved
0.5714	Remote Similarity	NPD8269	Approved
0.5714	Remote Similarity	NPD8267	Approved
0.5714	Remote Similarity	NPD8268	Approved
0.5714	Remote Similarity	NPD8266	Approved
0.5714	Remote Similarity	NPD7503	Approved
0.5702	Remote Similarity	NPD6648	Approved
0.5701	Remote Similarity	NPD4251	Approved
0.5701	Remote Similarity	NPD4250	Approved
0.5692	Remote Similarity	NPD6033	Approved
0.5688	Remote Similarity	NPD5692	Phase 3
0.5676	Remote Similarity	NPD7748	Approved
0.5667	Remote Similarity	NPD2067	Discontinued
0.5664	Remote Similarity	NPD7902	Approved
0.5659	Remote Similarity	NPD8273	Phase 1
0.5656	Remote Similarity	NPD4632	Approved
0.5641	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5694	Approved
0.5636	Remote Similarity	NPD6050	Approved
0.5636	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4822	Approved
0.5631	Remote Similarity	NPD4819	Approved
0.5631	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD5368	Approved
0.5631	Remote Similarity	NPD4821	Approved
0.5631	Remote Similarity	NPD4820	Approved
0.5625	Remote Similarity	NPD4629	Approved
0.5625	Remote Similarity	NPD5210	Approved
0.562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5330	Approved
0.5607	Remote Similarity	NPD7146	Approved
0.5607	Remote Similarity	NPD7521	Approved
0.5607	Remote Similarity	NPD7334	Approved
0.5607	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6684	Approved
0.5607	Remote Similarity	NPD5279	Phase 3
0.5607	Remote Similarity	NPD6409	Approved
0.5606	Remote Similarity	NPD6914	Discontinued
0.5603	Remote Similarity	NPD8084	Approved
0.5603	Remote Similarity	NPD8139	Approved
0.5603	Remote Similarity	NPD8083	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