NPASS Compound

Structure

NPC122056 OpenBabel07101719252D 33 38 0 0 1 0 0 0 0 0999 V2000 -7.1527 3.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 4.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 4.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7926 5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 4.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 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 -6.1235 6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0798 6.5428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 7.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 5.9190 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 15 1 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 23 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 16 2 1 1 0 0 0 16 19 1 0 0 0 0 17 13 1 1 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 20 26 1 6 0 0 0 21 27 1 6 0 0 0 22 16 1 1 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 28 1 1 0 0 0 24 33 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 10 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.27
Volume:	474.911
LogP:	4.288
LogD:	3.725
LogS:	-4.671
# Rotatable Bonds:	3
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	5.799
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	1.3717884030484129e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.856
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.333

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.626
Plasma Protein Binding (PPB):	82.3581314086914%
Volume Distribution (VD):	1.055
Pgp-substrate:	7.09091854095459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.307
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.318
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.774

ADMET: Excretion

Clearance (CL):	15.884
Half-life (T1/2):	0.513

ADMET: Toxicity

hERG Blockers:	0.693
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.883
Maximum Recommended Daily Dose:	0.321
Skin Sensitization:	0.914
Carcinogencity:	0.818
Eye Corrosion:	0.12
Eye Irritation:	0.216
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC122056

Natural Product ID:	NPC122056
*Common Name:**	Jaborosalactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PQCMITGKFWXOBO-GOXWLBPLSA-N
Standard InCHI:	InChI=1S/C28H38O5/c1-15-12-22(32-25(31)18(15)14-29)16(2)19-7-8-20-17-13-24-28(33-24)10-5-6-23(30)27(28,4)21(17)9-11-26(19,20)3/h5-6,16-17,19-22,24,29H,7-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,24+,26+,27-,28+/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]4[C@@]5(CC=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465075
PubChem CID:	12304656
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO18304	Jaborosa integrifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO18304	Jaborosa integrifolia	Species	Solanaceae	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
IC50	1
Others	5

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	0.68	uM	PMID[510435]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.29	uM	PMID[510435]
NPT2	Others	Unspecified		Ratio	=	6.3	n.a.	PMID[510435]
NPT27	Others	Unspecified		IC50	=	1830.0	nM	PMID[510435]
NPT2	Others	Unspecified		Ratio	=	2.7	n.a.	PMID[510435]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Inhibition	=	74.0	%	PMID[510436]

☑ 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 NPC122056 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	221
0.1-0.2	1243
0.2-0.3	3860
0.3-0.4	7995
0.4-0.5	13013
0.5-0.6	6690
0.6-0.7	6421
0.7-0.8	2858
0.8-0.85	300
0.85-0.9	63
0.9-0.95	23
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC286528
0.972	High Similarity	NPC167606
0.972	High Similarity	NPC140055
0.972	High Similarity	NPC20302
0.963	High Similarity	NPC50774
0.963	High Similarity	NPC709
0.9541	High Similarity	NPC264954
0.9537	High Similarity	NPC470493
0.9537	High Similarity	NPC183580
0.9537	High Similarity	NPC243065
0.9537	High Similarity	NPC312824
0.9537	High Similarity	NPC470492
0.9533	High Similarity	NPC67259
0.9533	High Similarity	NPC147912
0.9455	High Similarity	NPC474370
0.9434	High Similarity	NPC474315
0.9369	High Similarity	NPC67569
0.9286	High Similarity	NPC153700
0.9286	High Similarity	NPC470265
0.9286	High Similarity	NPC88326
0.9286	High Similarity	NPC23786
0.9238	High Similarity	NPC91034
0.9204	High Similarity	NPC469789
0.9189	High Similarity	NPC473274
0.9123	High Similarity	NPC8374
0.9123	High Similarity	NPC470494
0.9123	High Similarity	NPC3381
0.9123	High Similarity	NPC8369
0.9099	High Similarity	NPC186525
0.9091	High Similarity	NPC270929
0.9043	High Similarity	NPC293112
0.9035	High Similarity	NPC11895
0.9027	High Similarity	NPC470878
0.9027	High Similarity	NPC473256
0.9018	High Similarity	NPC476960
0.8991	High Similarity	NPC69291
0.8957	High Similarity	NPC81736
0.8957	High Similarity	NPC172154
0.8947	High Similarity	NPC170538
0.8929	High Similarity	NPC329736
0.8919	High Similarity	NPC64318
0.8899	High Similarity	NPC470960
0.887	High Similarity	NPC204812
0.885	High Similarity	NPC61520
0.885	High Similarity	NPC473270
0.8839	High Similarity	NPC476965
0.8839	High Similarity	NPC470959
0.8829	High Similarity	NPC284915
0.8818	High Similarity	NPC191620
0.8818	High Similarity	NPC476163
0.8814	High Similarity	NPC473593
0.8807	High Similarity	NPC29133
0.8796	High Similarity	NPC220155
0.8793	High Similarity	NPC241456
0.8793	High Similarity	NPC32868
0.8772	High Similarity	NPC476962
0.8727	High Similarity	NPC470961
0.8718	High Similarity	NPC473635
0.8684	High Similarity	NPC475520
0.8667	High Similarity	NPC476299
0.8667	High Similarity	NPC231240
0.8667	High Similarity	NPC474012
0.8654	High Similarity	NPC253826
0.8644	High Similarity	NPC156797
0.8636	High Similarity	NPC37116
0.8611	High Similarity	NPC266570
0.8609	High Similarity	NPC476961
0.8598	High Similarity	NPC475526
0.8598	High Similarity	NPC476237
0.8598	High Similarity	NPC72151
0.8598	High Similarity	NPC329345
0.8598	High Similarity	NPC473283
0.8598	High Similarity	NPC112009
0.8598	High Similarity	NPC297617
0.8595	High Similarity	NPC316915
0.8585	High Similarity	NPC282524
0.8571	High Similarity	NPC478056
0.8571	High Similarity	NPC98868
0.8571	High Similarity	NPC25909
0.8571	High Similarity	NPC316598
0.8545	High Similarity	NPC475941
0.8545	High Similarity	NPC474901
0.8545	High Similarity	NPC475065
0.8534	High Similarity	NPC46570
0.8532	High Similarity	NPC329048
0.8532	High Similarity	NPC475294
0.8532	High Similarity	NPC473284
0.8532	High Similarity	NPC330011
0.8522	High Similarity	NPC470495
0.8509	High Similarity	NPC239273
0.8505	High Similarity	NPC320447
0.8505	High Similarity	NPC155332
0.8505	High Similarity	NPC32577
0.8505	High Similarity	NPC136289
0.8505	High Similarity	NPC114540
0.8496	Intermediate Similarity	NPC238667
0.8496	Intermediate Similarity	NPC470953
0.8487	Intermediate Similarity	NPC287423
0.8482	Intermediate Similarity	NPC475524
0.8482	Intermediate Similarity	NPC475970
0.8482	Intermediate Similarity	NPC100267
0.8482	Intermediate Similarity	NPC236217
0.8462	Intermediate Similarity	NPC269642
0.8462	Intermediate Similarity	NPC107493
0.8455	Intermediate Similarity	NPC475418
0.8455	Intermediate Similarity	NPC318363
0.8455	Intermediate Similarity	NPC473482
0.8448	Intermediate Similarity	NPC268530
0.8448	Intermediate Similarity	NPC154491
0.844	Intermediate Similarity	NPC189863
0.8435	Intermediate Similarity	NPC311554
0.8435	Intermediate Similarity	NPC473720
0.8435	Intermediate Similarity	NPC257457
0.8426	Intermediate Similarity	NPC180204
0.8426	Intermediate Similarity	NPC475050
0.8426	Intermediate Similarity	NPC476889
0.8426	Intermediate Similarity	NPC95899
0.8426	Intermediate Similarity	NPC478057
0.8421	Intermediate Similarity	NPC148458
0.8417	Intermediate Similarity	NPC473620
0.8411	Intermediate Similarity	NPC224720
0.8411	Intermediate Similarity	NPC81530
0.8411	Intermediate Similarity	NPC115899
0.8411	Intermediate Similarity	NPC476240
0.8411	Intermediate Similarity	NPC476223
0.8396	Intermediate Similarity	NPC57079
0.8396	Intermediate Similarity	NPC108368
0.839	Intermediate Similarity	NPC120724
0.8381	Intermediate Similarity	NPC242848
0.8376	Intermediate Similarity	NPC159456
0.8376	Intermediate Similarity	NPC4021
0.8362	Intermediate Similarity	NPC42673
0.8362	Intermediate Similarity	NPC475041
0.8348	Intermediate Similarity	NPC55296
0.8348	Intermediate Similarity	NPC474518
0.8348	Intermediate Similarity	NPC476959
0.8348	Intermediate Similarity	NPC469684
0.8348	Intermediate Similarity	NPC471854
0.8347	Intermediate Similarity	NPC476966
0.8333	Intermediate Similarity	NPC474181
0.8333	Intermediate Similarity	NPC473253
0.8333	Intermediate Similarity	NPC476890
0.8333	Intermediate Similarity	NPC40918
0.8319	Intermediate Similarity	NPC90952
0.8319	Intermediate Similarity	NPC277769
0.8319	Intermediate Similarity	NPC285956
0.8318	Intermediate Similarity	NPC266955
0.8318	Intermediate Similarity	NPC476303
0.8318	Intermediate Similarity	NPC201406
0.8318	Intermediate Similarity	NPC476274
0.8304	Intermediate Similarity	NPC473627
0.8304	Intermediate Similarity	NPC16270
0.8302	Intermediate Similarity	NPC2049
0.8302	Intermediate Similarity	NPC108078
0.8302	Intermediate Similarity	NPC156546
0.8302	Intermediate Similarity	NPC126815
0.8291	Intermediate Similarity	NPC251226
0.8288	Intermediate Similarity	NPC322903
0.8288	Intermediate Similarity	NPC472825
0.8288	Intermediate Similarity	NPC177064
0.8286	Intermediate Similarity	NPC33473
0.8276	Intermediate Similarity	NPC146786
0.8276	Intermediate Similarity	NPC113448
0.8273	Intermediate Similarity	NPC60681
0.8261	Intermediate Similarity	NPC476963
0.8261	Intermediate Similarity	NPC470075
0.8257	Intermediate Similarity	NPC176883
0.8257	Intermediate Similarity	NPC247957
0.8257	Intermediate Similarity	NPC36688
0.8257	Intermediate Similarity	NPC26478
0.8257	Intermediate Similarity	NPC249187
0.8241	Intermediate Similarity	NPC235142
0.8241	Intermediate Similarity	NPC476897
0.8241	Intermediate Similarity	NPC310981
0.8241	Intermediate Similarity	NPC473514
0.8241	Intermediate Similarity	NPC93744
0.8241	Intermediate Similarity	NPC476888
0.8224	Intermediate Similarity	NPC252295
0.822	Intermediate Similarity	NPC470418
0.8214	Intermediate Similarity	NPC137911
0.8214	Intermediate Similarity	NPC5475
0.8214	Intermediate Similarity	NPC472216
0.8214	Intermediate Similarity	NPC173905
0.8214	Intermediate Similarity	NPC284828
0.8214	Intermediate Similarity	NPC228477
0.8208	Intermediate Similarity	NPC471153
0.8208	Intermediate Similarity	NPC195366
0.8208	Intermediate Similarity	NPC301534
0.8208	Intermediate Similarity	NPC250757
0.8208	Intermediate Similarity	NPC29152
0.8208	Intermediate Similarity	NPC114743
0.8205	Intermediate Similarity	NPC472933
0.8205	Intermediate Similarity	NPC230513
0.8198	Intermediate Similarity	NPC263729
0.8198	Intermediate Similarity	NPC472925
0.8198	Intermediate Similarity	NPC79298
0.8198	Intermediate Similarity	NPC43063
0.8198	Intermediate Similarity	NPC301666
0.8198	Intermediate Similarity	NPC470952
0.8197	Intermediate Similarity	NPC231529

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 NPC122056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1402
0.2-0.3	3496
0.3-0.4	2635
0.4-0.5	884
0.5-0.6	235
0.6-0.7	173
0.7-0.8	133
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.972	High Similarity	NPD7115	Discovery
0.8125	Intermediate Similarity	NPD6881	Approved
0.8125	Intermediate Similarity	NPD6899	Approved
0.807	Intermediate Similarity	NPD6649	Approved
0.807	Intermediate Similarity	NPD6650	Approved
0.8056	Intermediate Similarity	NPD4225	Approved
0.8036	Intermediate Similarity	NPD5697	Approved
0.7982	Intermediate Similarity	NPD7639	Approved
0.7982	Intermediate Similarity	NPD7290	Approved
0.7982	Intermediate Similarity	NPD7640	Approved
0.7982	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD6883	Approved
0.7946	Intermediate Similarity	NPD6675	Approved
0.7946	Intermediate Similarity	NPD6402	Approved
0.7946	Intermediate Similarity	NPD7128	Approved
0.7946	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD6399	Phase 3
0.7913	Intermediate Similarity	NPD6869	Approved
0.7913	Intermediate Similarity	NPD8130	Phase 1
0.7913	Intermediate Similarity	NPD6847	Approved
0.7913	Intermediate Similarity	NPD6617	Approved
0.7895	Intermediate Similarity	NPD6373	Approved
0.7895	Intermediate Similarity	NPD6013	Approved
0.7895	Intermediate Similarity	NPD6012	Approved
0.7895	Intermediate Similarity	NPD6372	Approved
0.7895	Intermediate Similarity	NPD6014	Approved
0.789	Intermediate Similarity	NPD7638	Approved
0.7845	Intermediate Similarity	NPD6882	Approved
0.7845	Intermediate Similarity	NPD8297	Approved
0.7838	Intermediate Similarity	NPD5211	Phase 2
0.783	Intermediate Similarity	NPD6079	Approved
0.7807	Intermediate Similarity	NPD7320	Approved
0.7807	Intermediate Similarity	NPD6011	Approved
0.7798	Intermediate Similarity	NPD6083	Phase 2
0.7798	Intermediate Similarity	NPD6084	Phase 2
0.7736	Intermediate Similarity	NPD5785	Approved
0.7719	Intermediate Similarity	NPD5701	Approved
0.7699	Intermediate Similarity	NPD5141	Approved
0.7692	Intermediate Similarity	NPD3618	Phase 1
0.7685	Intermediate Similarity	NPD7748	Approved
0.7664	Intermediate Similarity	NPD7515	Phase 2
0.7658	Intermediate Similarity	NPD5285	Approved
0.7658	Intermediate Similarity	NPD5286	Approved
0.7658	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5328	Approved
0.7636	Intermediate Similarity	NPD7902	Approved
0.7632	Intermediate Similarity	NPD6008	Approved
0.7615	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5696	Approved
0.7545	Intermediate Similarity	NPD5222	Approved
0.7545	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5221	Approved
0.7541	Intermediate Similarity	NPD6319	Approved
0.7524	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD5224	Approved
0.7522	Intermediate Similarity	NPD5225	Approved
0.7522	Intermediate Similarity	NPD5226	Approved
0.7522	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7477	Intermediate Similarity	NPD5173	Approved
0.7459	Intermediate Similarity	NPD7101	Approved
0.7459	Intermediate Similarity	NPD7100	Approved
0.7458	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5175	Approved
0.7456	Intermediate Similarity	NPD5174	Approved
0.7455	Intermediate Similarity	NPD4629	Approved
0.7455	Intermediate Similarity	NPD5210	Approved
0.7455	Intermediate Similarity	NPD5695	Phase 3
0.744	Intermediate Similarity	NPD7492	Approved
0.7436	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5223	Approved
0.7431	Intermediate Similarity	NPD4202	Approved
0.7429	Intermediate Similarity	NPD1694	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7398	Intermediate Similarity	NPD6054	Approved
0.7387	Intermediate Similarity	NPD4697	Phase 3
0.7383	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6672	Approved
0.7383	Intermediate Similarity	NPD5737	Approved
0.7381	Intermediate Similarity	NPD6616	Approved
0.7377	Intermediate Similarity	NPD6335	Approved
0.7373	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD7632	Discontinued
0.7364	Intermediate Similarity	NPD7900	Approved
0.7364	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6684	Approved
0.7358	Intermediate Similarity	NPD5330	Approved
0.7358	Intermediate Similarity	NPD7521	Approved
0.7358	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7146	Approved
0.7358	Intermediate Similarity	NPD7334	Approved
0.7355	Intermediate Similarity	NPD6868	Approved
0.7355	Intermediate Similarity	NPD6274	Approved
0.7345	Intermediate Similarity	NPD4700	Approved
0.7344	Intermediate Similarity	NPD7319	Approved
0.7339	Intermediate Similarity	NPD5693	Phase 1
0.7339	Intermediate Similarity	NPD8035	Phase 2
0.7339	Intermediate Similarity	NPD7637	Suspended
0.7339	Intermediate Similarity	NPD8034	Phase 2
0.7333	Intermediate Similarity	NPD4632	Approved
0.7323	Intermediate Similarity	NPD7078	Approved
0.7315	Intermediate Similarity	NPD4753	Phase 2
0.7308	Intermediate Similarity	NPD3667	Approved
0.7295	Intermediate Similarity	NPD6317	Approved
0.729	Intermediate Similarity	NPD3573	Approved
0.728	Intermediate Similarity	NPD6370	Approved
0.7264	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5363	Approved
0.725	Intermediate Similarity	NPD6053	Discontinued
0.7244	Intermediate Similarity	NPD7507	Approved
0.7236	Intermediate Similarity	NPD6314	Approved
0.7236	Intermediate Similarity	NPD6313	Approved
0.7227	Intermediate Similarity	NPD6371	Approved
0.7222	Intermediate Similarity	NPD7604	Phase 2
0.7222	Intermediate Similarity	NPD6903	Approved
0.7207	Intermediate Similarity	NPD6001	Approved
0.7203	Intermediate Similarity	NPD4730	Approved
0.7203	Intermediate Similarity	NPD4729	Approved
0.72	Intermediate Similarity	NPD7503	Approved
0.72	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD6015	Approved
0.7182	Intermediate Similarity	NPD5284	Approved
0.7182	Intermediate Similarity	NPD6411	Approved
0.7182	Intermediate Similarity	NPD5281	Approved
0.717	Intermediate Similarity	NPD3133	Approved
0.717	Intermediate Similarity	NPD3665	Phase 1
0.717	Intermediate Similarity	NPD3666	Approved
0.7156	Intermediate Similarity	NPD6673	Approved
0.7156	Intermediate Similarity	NPD6080	Approved
0.7156	Intermediate Similarity	NPD6904	Approved
0.7154	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5779	Approved
0.7117	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD5250	Approved
0.7083	Intermediate Similarity	NPD5249	Phase 3
0.7083	Intermediate Similarity	NPD5247	Approved
0.7083	Intermediate Similarity	NPD5251	Approved
0.7083	Intermediate Similarity	NPD5248	Approved
0.7063	Intermediate Similarity	NPD6909	Approved
0.7063	Intermediate Similarity	NPD5983	Phase 2
0.7063	Intermediate Similarity	NPD6908	Approved
0.7059	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD5128	Approved
0.7054	Intermediate Similarity	NPD8293	Discontinued
0.7034	Intermediate Similarity	NPD4767	Approved
0.7034	Intermediate Similarity	NPD4768	Approved
0.7025	Intermediate Similarity	NPD5217	Approved
0.7025	Intermediate Similarity	NPD5215	Approved
0.7025	Intermediate Similarity	NPD5216	Approved
0.7009	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5344	Discontinued
0.6981	Remote Similarity	NPD4223	Phase 3
0.6981	Remote Similarity	NPD4221	Approved
0.6981	Remote Similarity	NPD4270	Approved
0.6981	Remote Similarity	NPD4269	Approved
0.6977	Remote Similarity	NPD6336	Discontinued
0.6975	Remote Similarity	NPD6412	Phase 2
0.696	Remote Similarity	NPD7328	Approved
0.696	Remote Similarity	NPD7327	Approved
0.6944	Remote Similarity	NPD5329	Approved
0.6942	Remote Similarity	NPD5169	Approved
0.6942	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD5207	Approved
0.6929	Remote Similarity	NPD8513	Phase 3
0.6929	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5168	Approved
0.6909	Remote Similarity	NPD5208	Approved
0.6905	Remote Similarity	NPD7516	Approved
0.6887	Remote Similarity	NPD5369	Approved
0.6885	Remote Similarity	NPD5127	Approved
0.6881	Remote Similarity	NPD5690	Phase 2
0.6881	Remote Similarity	NPD5279	Phase 3
0.6881	Remote Similarity	NPD5786	Approved
0.6881	Remote Similarity	NPD6098	Approved
0.6881	Remote Similarity	NPD4623	Approved
0.6881	Remote Similarity	NPD4519	Discontinued
0.6875	Remote Similarity	NPD6050	Approved
0.6875	Remote Similarity	NPD5694	Approved
0.6852	Remote Similarity	NPD4197	Approved
0.6852	Remote Similarity	NPD3668	Phase 3
0.685	Remote Similarity	NPD8377	Approved
0.685	Remote Similarity	NPD8294	Approved
0.6822	Remote Similarity	NPD8328	Phase 3
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8379	Approved
0.6797	Remote Similarity	NPD8515	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