NPASS Compound

Structure

CID115786 OpenBabel06191715472D 24 26 0 0 1 0 0 0 0 0999 V2000 -2.1829 -3.5092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9761 -5.2288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4586 1.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4546 -2.4237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7782 -2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5831 -4.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -2.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -0.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5111 -1.0174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7110 -0.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5903 -4.1899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2752 -0.7650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 -4.9901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1972 -3.2704 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 8 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 10 14 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 16 1 0 0 0 0 13 23 1 6 0 0 0 14 15 1 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 16 11 1 6 0 0 0 16 17 1 0 0 0 0 17 24 1 1 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	337.007
LogP:	2.421
LogD:	1.648
LogS:	-3.705
# Rotatable Bonds:	3
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	4.792
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.847
MDCK Permeability:	2.063401734631043e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	91.01355743408203%
Volume Distribution (VD):	0.853
Pgp-substrate:	6.513453483581543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.39
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.875
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	7.366
Half-life (T1/2):	0.427

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.015
Drug-inuced Liver Injury (DILI):	0.884
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.922
Carcinogencity:	0.087
Eye Corrosion:	0.027
Eye Irritation:	0.213
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC115786

Natural Product ID:	NPC115786
*Common Name:**	2-Oxo-8Beta-Methacryloyloxyguaia-1(10),3,11(13)-Trien-12,6Alpha-Olide
IUPAC Name:	[(3aR,4R,9aS,9bR)-6,9-dimethyl-3-methylidene-2,7-dioxo-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-4-yl] 2-methylprop-2-enoate
Synonyms:
Standard InCHIKey:	KFNIILPAQWDAJK-XLNGHYISSA-N
Standard InCHI:	InChI=1S/C19H20O5/c1-8(2)18(21)23-13-7-10(4)14-12(20)6-9(3)15(14)17-16(13)11(5)19(22)24-17/h6,13,15-17H,1,5,7H2,2-4H3/t13-,15+,16-,17-/m1/s1
SMILES:	CC1=CC(=O)C2=C(C)C[C@H]([C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C)OC(=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL190211
PubChem CID:	636489
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	10.0	uM	PMID[458884]
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	pIC100	=	-1.0	n.a.	PMID[458884]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	10.0	uM	PMID[458885]

☑ 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 NPC115786 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	202
0.1-0.2	1328
0.2-0.3	5703
0.3-0.4	14252
0.4-0.5	10661
0.5-0.6	6554
0.6-0.7	3024
0.7-0.8	789
0.8-0.85	125
0.85-0.9	41
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC107787
0.9625	High Similarity	NPC78089
0.9487	High Similarity	NPC302426
0.9367	High Similarity	NPC301477
0.9367	High Similarity	NPC281949
0.9367	High Similarity	NPC255580
0.9367	High Similarity	NPC25684
0.9367	High Similarity	NPC39411
0.9125	High Similarity	NPC35089
0.9125	High Similarity	NPC10276
0.9103	High Similarity	NPC470240
0.9103	High Similarity	NPC476794
0.9059	High Similarity	NPC129419
0.9	High Similarity	NPC69271
0.9	High Similarity	NPC74673
0.8941	High Similarity	NPC268298
0.8875	High Similarity	NPC182550
0.8861	High Similarity	NPC195785
0.8861	High Similarity	NPC65603
0.8861	High Similarity	NPC15975
0.8846	High Similarity	NPC193351
0.8846	High Similarity	NPC138408
0.8846	High Similarity	NPC226669
0.8795	High Similarity	NPC165287
0.8765	High Similarity	NPC276356
0.875	High Similarity	NPC299235
0.8736	High Similarity	NPC123177
0.8736	High Similarity	NPC150978
0.8736	High Similarity	NPC70595
0.8736	High Similarity	NPC74103
0.869	High Similarity	NPC165162
0.8675	High Similarity	NPC39588
0.8675	High Similarity	NPC215294
0.8659	High Similarity	NPC141810
0.8642	High Similarity	NPC270126
0.8642	High Similarity	NPC472965
0.8642	High Similarity	NPC63649
0.8642	High Similarity	NPC617
0.8642	High Similarity	NPC264227
0.8621	High Similarity	NPC253144
0.8554	High Similarity	NPC173609
0.8539	High Similarity	NPC477131
0.8537	High Similarity	NPC223904
0.8523	High Similarity	NPC284185
0.8523	High Similarity	NPC133698
0.85	High Similarity	NPC123360
0.8488	Intermediate Similarity	NPC237540
0.8481	Intermediate Similarity	NPC476355
0.8471	Intermediate Similarity	NPC235792
0.8471	Intermediate Similarity	NPC33570
0.8471	Intermediate Similarity	NPC161957
0.8471	Intermediate Similarity	NPC21471
0.8452	Intermediate Similarity	NPC318468
0.8434	Intermediate Similarity	NPC471325
0.8415	Intermediate Similarity	NPC470239
0.8415	Intermediate Similarity	NPC178277
0.8415	Intermediate Similarity	NPC470244
0.8395	Intermediate Similarity	NPC97516
0.8395	Intermediate Similarity	NPC141789
0.8395	Intermediate Similarity	NPC476028
0.8395	Intermediate Similarity	NPC171204
0.8375	Intermediate Similarity	NPC155587
0.8372	Intermediate Similarity	NPC150755
0.8372	Intermediate Similarity	NPC475461
0.8372	Intermediate Similarity	NPC305475
0.8372	Intermediate Similarity	NPC64153
0.8353	Intermediate Similarity	NPC156485
0.8333	Intermediate Similarity	NPC198853
0.8333	Intermediate Similarity	NPC89555
0.8315	Intermediate Similarity	NPC131209
0.8313	Intermediate Similarity	NPC281132
0.8295	Intermediate Similarity	NPC4986
0.8293	Intermediate Similarity	NPC128276
0.8293	Intermediate Similarity	NPC472960
0.8272	Intermediate Similarity	NPC235906
0.8261	Intermediate Similarity	NPC169205
0.8256	Intermediate Similarity	NPC255307
0.825	Intermediate Similarity	NPC469643
0.825	Intermediate Similarity	NPC469641
0.825	Intermediate Similarity	NPC140287
0.8242	Intermediate Similarity	NPC193645
0.8242	Intermediate Similarity	NPC67584
0.8242	Intermediate Similarity	NPC48803
0.8242	Intermediate Similarity	NPC275960
0.8242	Intermediate Similarity	NPC90121
0.8242	Intermediate Similarity	NPC304886
0.8235	Intermediate Similarity	NPC54468
0.8235	Intermediate Similarity	NPC474703
0.8235	Intermediate Similarity	NPC475947
0.8228	Intermediate Similarity	NPC163003
0.8222	Intermediate Similarity	NPC135776
0.8182	Intermediate Similarity	NPC224652
0.8172	Intermediate Similarity	NPC141191
0.8172	Intermediate Similarity	NPC54843
0.8171	Intermediate Similarity	NPC41780
0.8171	Intermediate Similarity	NPC57744
0.8171	Intermediate Similarity	NPC187568
0.8161	Intermediate Similarity	NPC238593
0.8161	Intermediate Similarity	NPC104961
0.8161	Intermediate Similarity	NPC70422
0.8161	Intermediate Similarity	NPC50637
0.8161	Intermediate Similarity	NPC284902
0.8161	Intermediate Similarity	NPC70555
0.8152	Intermediate Similarity	NPC213078
0.8152	Intermediate Similarity	NPC185553
0.814	Intermediate Similarity	NPC114979
0.814	Intermediate Similarity	NPC191476
0.814	Intermediate Similarity	NPC141193
0.814	Intermediate Similarity	NPC96259
0.814	Intermediate Similarity	NPC159635
0.8132	Intermediate Similarity	NPC470010
0.8132	Intermediate Similarity	NPC323008
0.8132	Intermediate Similarity	NPC470013
0.8132	Intermediate Similarity	NPC167219
0.8132	Intermediate Similarity	NPC127019
0.8132	Intermediate Similarity	NPC262133
0.8125	Intermediate Similarity	NPC100487
0.8125	Intermediate Similarity	NPC472956
0.8118	Intermediate Similarity	NPC246076
0.8111	Intermediate Similarity	NPC261607
0.8111	Intermediate Similarity	NPC111114
0.8111	Intermediate Similarity	NPC300312
0.8101	Intermediate Similarity	NPC472955
0.809	Intermediate Similarity	NPC166919
0.8072	Intermediate Similarity	NPC108816
0.8072	Intermediate Similarity	NPC93763
0.8068	Intermediate Similarity	NPC475703
0.8065	Intermediate Similarity	NPC161493
0.8049	Intermediate Similarity	NPC472967
0.8049	Intermediate Similarity	NPC266159
0.8046	Intermediate Similarity	NPC215364
0.8043	Intermediate Similarity	NPC234339
0.8043	Intermediate Similarity	NPC52044
0.8043	Intermediate Similarity	NPC224689
0.8043	Intermediate Similarity	NPC213698
0.8043	Intermediate Similarity	NPC273197
0.8025	Intermediate Similarity	NPC320537
0.8025	Intermediate Similarity	NPC143979
0.8023	Intermediate Similarity	NPC272814
0.8023	Intermediate Similarity	NPC131669
0.8023	Intermediate Similarity	NPC40746
0.8023	Intermediate Similarity	NPC473390
0.8023	Intermediate Similarity	NPC169575
0.8	Intermediate Similarity	NPC144133
0.8	Intermediate Similarity	NPC470241
0.8	Intermediate Similarity	NPC150923
0.8	Intermediate Similarity	NPC42470
0.8	Intermediate Similarity	NPC179394
0.8	Intermediate Similarity	NPC62815
0.7978	Intermediate Similarity	NPC469628
0.7978	Intermediate Similarity	NPC475906
0.7978	Intermediate Similarity	NPC190718
0.7978	Intermediate Similarity	NPC91248
0.7978	Intermediate Similarity	NPC471047
0.7978	Intermediate Similarity	NPC469653
0.7978	Intermediate Similarity	NPC469631
0.7975	Intermediate Similarity	NPC476591
0.7975	Intermediate Similarity	NPC144511
0.7975	Intermediate Similarity	NPC88877
0.7975	Intermediate Similarity	NPC296522
0.7957	Intermediate Similarity	NPC299396
0.7957	Intermediate Similarity	NPC172998
0.7957	Intermediate Similarity	NPC301596
0.7955	Intermediate Similarity	NPC304558
0.7955	Intermediate Similarity	NPC38576
0.7955	Intermediate Similarity	NPC236692
0.7955	Intermediate Similarity	NPC67493
0.7955	Intermediate Similarity	NPC279859
0.7955	Intermediate Similarity	NPC309757
0.7952	Intermediate Similarity	NPC208223
0.7935	Intermediate Similarity	NPC474338
0.7935	Intermediate Similarity	NPC473330
0.7935	Intermediate Similarity	NPC473316
0.7935	Intermediate Similarity	NPC140543
0.7931	Intermediate Similarity	NPC476804
0.7927	Intermediate Similarity	NPC244166
0.7917	Intermediate Similarity	NPC86077
0.7912	Intermediate Similarity	NPC475925
0.7907	Intermediate Similarity	NPC229825
0.7907	Intermediate Similarity	NPC35556
0.7901	Intermediate Similarity	NPC295633
0.7901	Intermediate Similarity	NPC58956
0.7901	Intermediate Similarity	NPC269206
0.7889	Intermediate Similarity	NPC32922
0.7889	Intermediate Similarity	NPC151770
0.7889	Intermediate Similarity	NPC295312
0.7882	Intermediate Similarity	NPC290508
0.7882	Intermediate Similarity	NPC73052
0.7882	Intermediate Similarity	NPC6823
0.7882	Intermediate Similarity	NPC293418
0.7865	Intermediate Similarity	NPC160138
0.7865	Intermediate Similarity	NPC24728
0.7865	Intermediate Similarity	NPC72513
0.7865	Intermediate Similarity	NPC231889
0.7849	Intermediate Similarity	NPC170120
0.7848	Intermediate Similarity	NPC470256
0.7841	Intermediate Similarity	NPC470755
0.7831	Intermediate Similarity	NPC472959
0.7826	Intermediate Similarity	NPC469692
0.7826	Intermediate Similarity	NPC475838

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 NPC115786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1889
0.2-0.3	3975
0.3-0.4	2128
0.4-0.5	620
0.5-0.6	270
0.6-0.7	73
0.7-0.8	9
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD1695	Approved
0.8242	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1694	Approved
0.7303	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5785	Approved
0.7222	Intermediate Similarity	NPD7154	Phase 3
0.7212	Intermediate Similarity	NPD6371	Approved
0.7111	Intermediate Similarity	NPD5209	Approved
0.7065	Intermediate Similarity	NPD5363	Approved
0.7053	Intermediate Similarity	NPD6698	Approved
0.7053	Intermediate Similarity	NPD46	Approved
0.7033	Intermediate Similarity	NPD5362	Discontinued
0.701	Intermediate Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD6435	Approved
0.6882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6903	Approved
0.6829	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD7521	Approved
0.6809	Remote Similarity	NPD6409	Approved
0.6809	Remote Similarity	NPD7334	Approved
0.6809	Remote Similarity	NPD5330	Approved
0.6809	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD4269	Approved
0.6739	Remote Similarity	NPD4270	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.6733	Remote Similarity	NPD4225	Approved
0.6703	Remote Similarity	NPD5368	Approved
0.6703	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6633	Remote Similarity	NPD5693	Phase 1
0.6632	Remote Similarity	NPD5786	Approved
0.6632	Remote Similarity	NPD4249	Approved
0.6606	Remote Similarity	NPD6053	Discontinued
0.66	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4251	Approved
0.6562	Remote Similarity	NPD4250	Approved
0.6531	Remote Similarity	NPD5207	Approved
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4252	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6517	Remote Similarity	NPD8039	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD4268	Approved
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6408	Remote Similarity	NPD5696	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6372	Remote Similarity	NPD7115	Discovery
0.6337	Remote Similarity	NPD6001	Approved
0.6316	Remote Similarity	NPD5332	Approved
0.6316	Remote Similarity	NPD5331	Approved
0.6311	Remote Similarity	NPD6083	Phase 2
0.6311	Remote Similarity	NPD7902	Approved
0.6311	Remote Similarity	NPD6084	Phase 2
0.63	Remote Similarity	NPD7983	Approved
0.6296	Remote Similarity	NPD5697	Approved
0.6277	Remote Similarity	NPD4790	Discontinued
0.6263	Remote Similarity	NPD6673	Approved
0.6263	Remote Similarity	NPD6080	Approved
0.6263	Remote Similarity	NPD6101	Approved
0.6263	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7638	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6238	Remote Similarity	NPD5779	Approved
0.6238	Remote Similarity	NPD5778	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6216	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD5692	Phase 3
0.6196	Remote Similarity	NPD4756	Discovery
0.619	Remote Similarity	NPD7639	Approved
0.619	Remote Similarity	NPD7640	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD5208	Approved
0.6147	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD5284	Approved
0.6139	Remote Similarity	NPD6050	Approved
0.6139	Remote Similarity	NPD5694	Approved
0.6139	Remote Similarity	NPD5281	Approved
0.6139	Remote Similarity	NPD6411	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.6091	Remote Similarity	NPD6011	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3666	Approved
0.6082	Remote Similarity	NPD3668	Phase 3
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6061	Remote Similarity	NPD3573	Approved
0.6042	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD6648	Approved
0.6019	Remote Similarity	NPD6052	Approved
0.6018	Remote Similarity	NPD8297	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4695	Discontinued
0.5982	Remote Similarity	NPD2067	Discontinued
0.5981	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD7515	Phase 2
0.5977	Remote Similarity	NPD7331	Phase 2
0.5977	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD5210	Approved
0.5962	Remote Similarity	NPD4629	Approved
0.596	Remote Similarity	NPD6422	Discontinued
0.596	Remote Similarity	NPD5279	Phase 3
0.596	Remote Similarity	NPD6098	Approved
0.5941	Remote Similarity	NPD4753	Phase 2
0.5941	Remote Similarity	NPD5370	Suspended
0.5941	Remote Similarity	NPD6051	Approved
0.5929	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5211	Phase 2
0.5918	Remote Similarity	NPD4786	Approved
0.5905	Remote Similarity	NPD7839	Suspended
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5882	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7341	Phase 2
0.5862	Remote Similarity	NPD6274	Approved
0.5856	Remote Similarity	NPD6412	Phase 2
0.5849	Remote Similarity	NPD4755	Approved
0.5841	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD8035	Phase 2
0.5825	Remote Similarity	NPD8034	Phase 2
0.5825	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7637	Suspended
0.5825	Remote Similarity	NPD6079	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5814	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5654	Approved
0.58	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5328	Approved
0.578	Remote Similarity	NPD5224	Approved
0.578	Remote Similarity	NPD5225	Approved
0.578	Remote Similarity	NPD5226	Approved
0.578	Remote Similarity	NPD4633	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5755	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4697	Phase 3
0.5755	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD5221	Approved
0.5755	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4700	Approved
0.5738	Remote Similarity	NPD7492	Approved
0.5727	Remote Similarity	NPD6647	Phase 2
0.5727	Remote Similarity	NPD5175	Approved
0.5727	Remote Similarity	NPD5174	Approved
0.5714	Remote Similarity	NPD4223	Phase 3
0.5714	Remote Similarity	NPD4691	Approved
0.5714	Remote Similarity	NPD7101	Approved
0.5714	Remote Similarity	NPD4221	Approved
0.5714	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD6614	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7100	Approved
0.5701	Remote Similarity	NPD5959	Approved
0.5701	Remote Similarity	NPD5173	Approved
0.5691	Remote Similarity	NPD7507	Approved
0.5691	Remote Similarity	NPD6616	Approved
0.569	Remote Similarity	NPD4632	Approved
0.5688	Remote Similarity	NPD5223	Approved
0.5682	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6317	Approved
0.5669	Remote Similarity	NPD6845	Suspended
0.5667	Remote Similarity	NPD6054	Approved
0.5667	Remote Similarity	NPD229	Approved
0.5667	Remote Similarity	NPD6319	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