NPASS Compound

Structure

NPC19087 OpenBabel07101719512D 25 27 0 0 1 0 0 0 0 0999 V2000 -1.8370 3.7992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2475 3.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9297 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2410 1.2937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2560 3.1923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5430 5.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2371 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4385 4.3537 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 1.2946 0.9705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6978 2.1115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9002 1.0288 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5068 2.5457 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2910 1.1979 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4769 1.5461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3232 0.9463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5249 3.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9999 0.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4565 5.7550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 0.6220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7159 4.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4204 2.9524 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 9 2 0 0 0 0 3 10 2 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 11 4 1 6 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 6 1 1 0 0 0 12 15 1 0 0 0 0 13 21 1 6 0 0 0 14 16 1 0 0 0 0 14 24 1 6 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	351.07
LogP:	0.555
LogD:	0.759
LogS:	-2.228
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	5.052
Fsp3:	0.579
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:	-5.197
MDCK Permeability:	0.00018072643433697522
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	60.326988220214844%
Volume Distribution (VD):	0.625
Pgp-substrate:	48.64957809448242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.29
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	4.97
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.182
Carcinogencity:	0.086
Eye Corrosion:	0.012
Eye Irritation:	0.067
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC19087

Natural Product ID:	NPC19087
*Common Name:**	3Alpha,8Alphadihydroxy-1Alphah,5Alphah,6Betah,7Alphah,11Betah-Guai-4(15),10(14)-Dien-6,12-Olide 8-O-2-Hydroxymethylacrylate
IUPAC Name:	[(3S,3aR,4S,6aR,8R,9aR,9bR)-8-hydroxy-3-methyl-6,9-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	CCBNOSMFTUQQLZ-OPCFMFSHSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h11-17,20-21H,1-3,5-7H2,4H3/t11-,12-,13+,14-,15-,16+,17+/m0/s1
SMILES:	OCC(=C)C(=O)O[C@H]1CC(=C)[C@H]2[C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)C(=C)[C@@H](C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517322
PubChem CID:	11360021
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921425]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9587	Saussurea laniceps	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	8

Activity Type	# Activity
NON-MOLECULAR	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	46.33	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	43.75	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	13.44	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.03	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	24.27	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	29.8	cpm	PMID[554322]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	34.94	cpm	PMID[554322]

☑ 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 NPC19087 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	240
0.1-0.2	1710
0.2-0.3	6046
0.3-0.4	14072
0.4-0.5	10552
0.5-0.6	6861
0.6-0.7	2557
0.7-0.8	517
0.8-0.85	60
0.85-0.9	47
0.9-0.95	29
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC184063
0.9881	High Similarity	NPC38392
0.9762	High Similarity	NPC217983
0.9762	High Similarity	NPC207114
0.9524	High Similarity	NPC187661
0.9333	High Similarity	NPC474313
0.931	High Similarity	NPC54065
0.931	High Similarity	NPC297474
0.9294	High Similarity	NPC304558
0.9286	High Similarity	NPC194859
0.9286	High Similarity	NPC224386
0.9222	High Similarity	NPC142529
0.9222	High Similarity	NPC91771
0.9205	High Similarity	NPC35959
0.9205	High Similarity	NPC475925
0.9205	High Similarity	NPC29821
0.9205	High Similarity	NPC57304
0.9205	High Similarity	NPC63193
0.9205	High Similarity	NPC171360
0.9205	High Similarity	NPC133888
0.9205	High Similarity	NPC293001
0.9195	High Similarity	NPC215556
0.9195	High Similarity	NPC155935
0.9167	High Similarity	NPC128246
0.9091	High Similarity	NPC216284
0.9091	High Similarity	NPC35809
0.908	High Similarity	NPC79549
0.9048	High Similarity	NPC246076
0.9	High Similarity	NPC473331
0.8929	High Similarity	NPC126248
0.8913	High Similarity	NPC311904
0.8901	High Similarity	NPC476053
0.8901	High Similarity	NPC472873
0.8889	High Similarity	NPC258216
0.8889	High Similarity	NPC60386
0.8889	High Similarity	NPC473234
0.8889	High Similarity	NPC473263
0.8889	High Similarity	NPC473273
0.8889	High Similarity	NPC308656
0.8889	High Similarity	NPC200237
0.8889	High Similarity	NPC475788
0.8851	High Similarity	NPC56593
0.883	High Similarity	NPC171759
0.8804	High Similarity	NPC18019
0.8804	High Similarity	NPC24956
0.8791	High Similarity	NPC198853
0.8778	High Similarity	NPC286341
0.8778	High Similarity	NPC191339
0.8778	High Similarity	NPC155215
0.8764	High Similarity	NPC12872
0.8764	High Similarity	NPC168679
0.875	High Similarity	NPC118601
0.875	High Similarity	NPC24728
0.8736	High Similarity	NPC300082
0.8736	High Similarity	NPC284534
0.8736	High Similarity	NPC204105
0.8721	High Similarity	NPC111409
0.871	High Similarity	NPC471150
0.8696	High Similarity	NPC170120
0.8696	High Similarity	NPC213698
0.8696	High Similarity	NPC163228
0.8681	High Similarity	NPC153590
0.8652	High Similarity	NPC471149
0.8652	High Similarity	NPC178875
0.8636	High Similarity	NPC64153
0.8636	High Similarity	NPC236692
0.8636	High Similarity	NPC309757
0.8587	High Similarity	NPC262133
0.8587	High Similarity	NPC127019
0.8587	High Similarity	NPC470013
0.8587	High Similarity	NPC470010
0.8587	High Similarity	NPC323008
0.8571	High Similarity	NPC133698
0.8571	High Similarity	NPC131209
0.8556	High Similarity	NPC283409
0.8556	High Similarity	NPC472872
0.8539	High Similarity	NPC201658
0.8511	High Similarity	NPC161493
0.8511	High Similarity	NPC108475
0.8511	High Similarity	NPC170143
0.8511	High Similarity	NPC213947
0.8506	High Similarity	NPC245665
0.8495	Intermediate Similarity	NPC67584
0.8495	Intermediate Similarity	NPC52044
0.8495	Intermediate Similarity	NPC304886
0.8469	Intermediate Similarity	NPC44004
0.8438	Intermediate Similarity	NPC150923
0.8427	Intermediate Similarity	NPC238593
0.8427	Intermediate Similarity	NPC470242
0.8421	Intermediate Similarity	NPC49833
0.8421	Intermediate Similarity	NPC249171
0.8404	Intermediate Similarity	NPC476009
0.8404	Intermediate Similarity	NPC126156
0.8404	Intermediate Similarity	NPC213078
0.8387	Intermediate Similarity	NPC477131
0.8351	Intermediate Similarity	NPC80144
0.8333	Intermediate Similarity	NPC471381
0.8333	Intermediate Similarity	NPC186861
0.8316	Intermediate Similarity	NPC304445
0.8316	Intermediate Similarity	NPC181151
0.8316	Intermediate Similarity	NPC236580
0.8298	Intermediate Similarity	NPC475900
0.8265	Intermediate Similarity	NPC473148
0.8256	Intermediate Similarity	NPC19841
0.8247	Intermediate Similarity	NPC67296
0.8242	Intermediate Similarity	NPC91248
0.8229	Intermediate Similarity	NPC221615
0.8229	Intermediate Similarity	NPC45125
0.8222	Intermediate Similarity	NPC67493
0.8222	Intermediate Similarity	NPC162071
0.8211	Intermediate Similarity	NPC474297
0.8163	Intermediate Similarity	NPC86077
0.8161	Intermediate Similarity	NPC51507
0.8161	Intermediate Similarity	NPC156658
0.8161	Intermediate Similarity	NPC258965
0.8161	Intermediate Similarity	NPC6823
0.8132	Intermediate Similarity	NPC190753
0.8132	Intermediate Similarity	NPC270270
0.8132	Intermediate Similarity	NPC186148
0.8125	Intermediate Similarity	NPC169205
0.8111	Intermediate Similarity	NPC235792
0.8105	Intermediate Similarity	NPC167893
0.81	Intermediate Similarity	NPC54737
0.8095	Intermediate Similarity	NPC143979
0.8095	Intermediate Similarity	NPC320537
0.809	Intermediate Similarity	NPC54468
0.8085	Intermediate Similarity	NPC135776
0.8085	Intermediate Similarity	NPC472874
0.8065	Intermediate Similarity	NPC474323
0.8065	Intermediate Similarity	NPC37607
0.8065	Intermediate Similarity	NPC301969
0.8065	Intermediate Similarity	NPC206614
0.8043	Intermediate Similarity	NPC177629
0.8043	Intermediate Similarity	NPC224652
0.8043	Intermediate Similarity	NPC58219
0.8041	Intermediate Similarity	NPC141191
0.8021	Intermediate Similarity	NPC230800
0.8021	Intermediate Similarity	NPC185553
0.802	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC156485
0.8	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC203659
0.798	Intermediate Similarity	NPC474747
0.798	Intermediate Similarity	NPC225353
0.7959	Intermediate Similarity	NPC70865
0.7957	Intermediate Similarity	NPC92974
0.7957	Intermediate Similarity	NPC4986
0.7957	Intermediate Similarity	NPC295312
0.7941	Intermediate Similarity	NPC68248
0.7938	Intermediate Similarity	NPC477949
0.7921	Intermediate Similarity	NPC166115
0.7921	Intermediate Similarity	NPC243998
0.7917	Intermediate Similarity	NPC469873
0.7917	Intermediate Similarity	NPC48803
0.7917	Intermediate Similarity	NPC275960
0.7917	Intermediate Similarity	NPC90121
0.7917	Intermediate Similarity	NPC193645
0.7912	Intermediate Similarity	NPC165162
0.7912	Intermediate Similarity	NPC255307
0.79	Intermediate Similarity	NPC475945
0.79	Intermediate Similarity	NPC475871
0.79	Intermediate Similarity	NPC110989
0.7895	Intermediate Similarity	NPC475912
0.7895	Intermediate Similarity	NPC475838
0.7895	Intermediate Similarity	NPC125674
0.7895	Intermediate Similarity	NPC228451
0.7882	Intermediate Similarity	NPC48641
0.7879	Intermediate Similarity	NPC308824
0.7872	Intermediate Similarity	NPC71533
0.7872	Intermediate Similarity	NPC129419
0.7872	Intermediate Similarity	NPC475855
0.7872	Intermediate Similarity	NPC106510
0.7872	Intermediate Similarity	NPC246173
0.7865	Intermediate Similarity	NPC47635
0.7864	Intermediate Similarity	NPC59489
0.7864	Intermediate Similarity	NPC139838
0.7849	Intermediate Similarity	NPC476805
0.7849	Intermediate Similarity	NPC202672
0.7849	Intermediate Similarity	NPC476803
0.7835	Intermediate Similarity	NPC470883
0.7835	Intermediate Similarity	NPC39859
0.7835	Intermediate Similarity	NPC76862
0.7835	Intermediate Similarity	NPC158416
0.7835	Intermediate Similarity	NPC284518
0.7826	Intermediate Similarity	NPC475461
0.7826	Intermediate Similarity	NPC474949
0.7826	Intermediate Similarity	NPC305475
0.7826	Intermediate Similarity	NPC475019
0.7816	Intermediate Similarity	NPC208223
0.7812	Intermediate Similarity	NPC474247
0.7812	Intermediate Similarity	NPC474338
0.7812	Intermediate Similarity	NPC167219
0.7802	Intermediate Similarity	NPC158756
0.7802	Intermediate Similarity	NPC191476
0.7802	Intermediate Similarity	NPC476804
0.7802	Intermediate Similarity	NPC474780
0.7802	Intermediate Similarity	NPC114979
0.78	Intermediate Similarity	NPC164551
0.7789	Intermediate Similarity	NPC184463
0.7789	Intermediate Similarity	NPC208886

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 NPC19087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	2450
0.2-0.3	3860
0.3-0.4	1756
0.4-0.5	490
0.5-0.6	252
0.6-0.7	32
0.7-0.8	11
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
0.802	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD1695	Approved
0.7917	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD5785	Approved
0.7447	Intermediate Similarity	NPD4249	Approved
0.7368	Intermediate Similarity	NPD4250	Approved
0.7368	Intermediate Similarity	NPD4251	Approved
0.734	Intermediate Similarity	NPD5363	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7128	Intermediate Similarity	NPD5362	Discontinued
0.7097	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6989	Remote Similarity	NPD4252	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD7154	Phase 3
0.6931	Remote Similarity	NPD5282	Discontinued
0.69	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD6435	Approved
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6827	Remote Similarity	NPD4225	Approved
0.6809	Remote Similarity	NPD4819	Approved
0.6809	Remote Similarity	NPD4820	Approved
0.6809	Remote Similarity	NPD4821	Approved
0.6809	Remote Similarity	NPD4822	Approved
0.6804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD4268	Approved
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD7838	Discovery
0.6632	Remote Similarity	NPD5368	Approved
0.6598	Remote Similarity	NPD5332	Approved
0.6598	Remote Similarity	NPD5331	Approved
0.6569	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD4790	Discontinued
0.6486	Remote Similarity	NPD6686	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4238	Approved
0.6421	Remote Similarity	NPD4802	Phase 2
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6355	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6399	Phase 3
0.633	Remote Similarity	NPD7632	Discontinued
0.6321	Remote Similarity	NPD7839	Suspended
0.6306	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD8515	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8517	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD5344	Discontinued
0.623	Remote Similarity	NPD7492	Approved
0.6207	Remote Similarity	NPD8133	Approved
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6163	Remote Similarity	NPD3198	Approved
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7319	Approved
0.6139	Remote Similarity	NPD1694	Approved
0.6129	Remote Similarity	NPD7078	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD8268	Approved
0.6116	Remote Similarity	NPD8269	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD8267	Approved
0.6116	Remote Similarity	NPD8266	Approved
0.6111	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD5697	Approved
0.6106	Remote Similarity	NPD6412	Phase 2
0.608	Remote Similarity	NPD7736	Approved
0.6075	Remote Similarity	NPD5695	Phase 3
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD6370	Approved
0.6058	Remote Similarity	NPD5370	Suspended
0.6055	Remote Similarity	NPD5696	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6053	Remote Similarity	NPD7320	Approved
0.6048	Remote Similarity	NPD7507	Approved
0.604	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6650	Approved
0.6034	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6059	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5701	Approved
0.5962	Remote Similarity	NPD6903	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5943	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4788	Approved
0.5941	Remote Similarity	NPD6695	Phase 3
0.5932	Remote Similarity	NPD4632	Approved
0.5929	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7521	Approved
0.5922	Remote Similarity	NPD7146	Approved
0.5922	Remote Similarity	NPD6409	Approved
0.5922	Remote Similarity	NPD5330	Approved
0.5922	Remote Similarity	NPD6684	Approved
0.5922	Remote Similarity	NPD7334	Approved
0.592	Remote Similarity	NPD8273	Phase 1
0.5913	Remote Similarity	NPD6011	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD3666	Approved
0.5882	Remote Similarity	NPD3133	Approved
0.5882	Remote Similarity	NPD3665	Phase 1
0.5859	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8297	Approved
0.5847	Remote Similarity	NPD6882	Approved
0.5842	Remote Similarity	NPD3667	Approved
0.5826	Remote Similarity	NPD6685	Approved
0.5824	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD4634	Approved
0.581	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD229	Approved
0.5804	Remote Similarity	NPD1700	Approved
0.5794	Remote Similarity	NPD5281	Approved
0.5794	Remote Similarity	NPD5693	Phase 1
0.5794	Remote Similarity	NPD5284	Approved
0.5789	Remote Similarity	NPD5141	Approved
0.5785	Remote Similarity	NPD6009	Approved
0.578	Remote Similarity	NPD4629	Approved
0.578	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5210	Approved
0.5769	Remote Similarity	NPD6845	Suspended
0.5769	Remote Similarity	NPD3618	Phase 1
0.5755	Remote Similarity	NPD4753	Phase 2
0.5738	Remote Similarity	NPD7327	Approved
0.5738	Remote Similarity	NPD7328	Approved
0.5736	Remote Similarity	NPD5956	Approved
0.5728	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4786	Approved
0.5726	Remote Similarity	NPD5983	Phase 2
0.5726	Remote Similarity	NPD8033	Approved
0.5726	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7524	Approved
0.5714	Remote Similarity	NPD7750	Discontinued
0.5714	Remote Similarity	NPD5285	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5702	Remote Similarity	NPD6274	Approved
0.5701	Remote Similarity	NPD5207	Approved
0.57	Remote Similarity	NPD6929	Approved
0.5692	Remote Similarity	NPD7260	Phase 2
0.5691	Remote Similarity	NPD7516	Approved
0.569	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6420	Discontinued
0.5676	Remote Similarity	NPD4755	Approved
0.5676	Remote Similarity	NPD7902	Approved
0.566	Remote Similarity	NPD5737	Approved
0.566	Remote Similarity	NPD6672	Approved
0.5645	Remote Similarity	NPD8377	Approved
0.5645	Remote Similarity	NPD8294	Approved
0.5644	Remote Similarity	NPD6931	Approved
0.5644	Remote Similarity	NPD6930	Phase 2
0.5635	Remote Similarity	NPD7829	Approved
0.5635	Remote Similarity	NPD7604	Phase 2
0.5635	Remote Similarity	NPD7830	Approved
0.5635	Remote Similarity	NPD7642	Approved
0.563	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.563	Remote Similarity	NPD2204	Approved
0.5619	Remote Similarity	NPD5279	Phase 3
0.5619	Remote Similarity	NPD3574	Clinical (unspecified phase)

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