NPASS Compound

Structure

NPC9274 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 1.4164 -5.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 -3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 -5.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 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 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 4.3301 0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 -4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 -4.6974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 0 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 2 0 0 0 0 6 21 1 0 0 0 0 7 30 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 30 1 0 0 0 0 17 27 1 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 19 26 1 0 0 0 0 21 22 2 0 0 0 0 22 23 1 0 0 0 0 23 25 2 0 0 0 0 24 11 1 1 0 0 0 24 28 1 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 26 32 2 0 0 0 0 27 28 1 0 0 0 0 27 33 1 6 0 0 0 28 30 1 1 0 0 0 29 34 2 0 0 0 0 29 35 1 0 0 0 0 30 31 1 1 0 0 0 31 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.34
Volume:	538.405
LogP:	5.406
LogD:	3.929
LogS:	-4.938
# Rotatable Bonds:	10
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.576
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.178
MDCK Permeability:	1.892407817649655e-05
Pgp-inhibitor:	0.232
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.816

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	97.93828582763672%
Volume Distribution (VD):	0.475
Pgp-substrate:	1.4384044408798218%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.748
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	1.522
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.645
Drug-inuced Liver Injury (DILI):	0.602
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.026
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.441

Download Data

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

Natural Product: NPC9274

Natural Product ID:	NPC9274
*Common Name:**	Daedaleanic Acid A
IUPAC Name:	(2R)-2-[(2R,3R,3aR,9bR)-2-hydroxy-3a,7,9b-trimethyl-6-(4-methyl-3-oxopentyl)-2,3,4,5-tetrahydro-1H-cyclopenta[a]naphthalen-3-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	MFOKWUZMHJXWFI-ZKBPDDLLSA-N
Standard InCHI:	InChI=1S/C31H46O4/c1-18(2)20(5)9-11-24(29(34)35)28-27(33)17-31(8)25-13-10-21(6)22(12-14-26(32)19(3)4)23(25)15-16-30(28,31)7/h10,13,18-19,24,27-28,33H,5,9,11-12,14-17H2,1-4,6-8H3,(H,34,35)/t24-,27-,28+,30-,31+/m1/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2(C)c3ccc(C)c(CCC(=O)C(C)C)c3CC[C@]12C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456728
PubChem CID:	11179164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32674	daedalea dickisii	Species	Coriolaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15974617]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	36000.0	nM	PMID[533618]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	206000.0	nM	PMID[533618]

☑ 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 NPC9274 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	200
0.1-0.2	769
0.2-0.3	1973
0.3-0.4	5926
0.4-0.5	16210
0.5-0.6	14759
0.6-0.7	2552
0.7-0.8	292
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.856	High Similarity	NPC159811
0.8519	High Similarity	NPC225079
0.8468	Intermediate Similarity	NPC142326
0.8468	Intermediate Similarity	NPC94751
0.8468	Intermediate Similarity	NPC244933
0.8468	Intermediate Similarity	NPC85560
0.8393	Intermediate Similarity	NPC21929
0.8378	Intermediate Similarity	NPC471186
0.8349	Intermediate Similarity	NPC133809
0.8349	Intermediate Similarity	NPC136810
0.8349	Intermediate Similarity	NPC264728
0.8349	Intermediate Similarity	NPC128248
0.8319	Intermediate Similarity	NPC202015
0.8241	Intermediate Similarity	NPC226041
0.8165	Intermediate Similarity	NPC120393
0.8103	Intermediate Similarity	NPC471188
0.8103	Intermediate Similarity	NPC471189
0.8091	Intermediate Similarity	NPC221825
0.8073	Intermediate Similarity	NPC469891
0.8073	Intermediate Similarity	NPC469892
0.8073	Intermediate Similarity	NPC469890
0.807	Intermediate Similarity	NPC112903
0.8067	Intermediate Similarity	NPC212891
0.8053	Intermediate Similarity	NPC321670
0.8017	Intermediate Similarity	NPC265513
0.7982	Intermediate Similarity	NPC37914
0.7982	Intermediate Similarity	NPC469893
0.7982	Intermediate Similarity	NPC185763
0.7982	Intermediate Similarity	NPC83409
0.7965	Intermediate Similarity	NPC56168
0.7917	Intermediate Similarity	NPC105141
0.7917	Intermediate Similarity	NPC242764
0.7881	Intermediate Similarity	NPC470253
0.7881	Intermediate Similarity	NPC287055
0.7881	Intermediate Similarity	NPC93287
0.7881	Intermediate Similarity	NPC242957
0.7881	Intermediate Similarity	NPC306977
0.7881	Intermediate Similarity	NPC206414
0.7863	Intermediate Similarity	NPC95126
0.7863	Intermediate Similarity	NPC475002
0.7857	Intermediate Similarity	NPC477366
0.7851	Intermediate Similarity	NPC45794
0.784	Intermediate Similarity	NPC328107
0.7823	Intermediate Similarity	NPC369
0.7823	Intermediate Similarity	NPC293831
0.7805	Intermediate Similarity	NPC133302
0.7805	Intermediate Similarity	NPC183339
0.7805	Intermediate Similarity	NPC234337
0.7805	Intermediate Similarity	NPC133389
0.7795	Intermediate Similarity	NPC477365
0.7787	Intermediate Similarity	NPC254233
0.7761	Intermediate Similarity	NPC473440
0.776	Intermediate Similarity	NPC273336
0.776	Intermediate Similarity	NPC182333
0.775	Intermediate Similarity	NPC215419
0.775	Intermediate Similarity	NPC221275
0.7734	Intermediate Similarity	NPC51448
0.7734	Intermediate Similarity	NPC477370
0.7734	Intermediate Similarity	NPC115797
0.7724	Intermediate Similarity	NPC472708
0.7724	Intermediate Similarity	NPC476645
0.7717	Intermediate Similarity	NPC477363
0.7705	Intermediate Similarity	NPC323440
0.7705	Intermediate Similarity	NPC222968
0.7705	Intermediate Similarity	NPC80605
0.7698	Intermediate Similarity	NPC477362
0.7698	Intermediate Similarity	NPC77691
0.768	Intermediate Similarity	NPC18785
0.7674	Intermediate Similarity	NPC37968
0.7667	Intermediate Similarity	NPC471721
0.7667	Intermediate Similarity	NPC294458
0.7656	Intermediate Similarity	NPC477357
0.7656	Intermediate Similarity	NPC269598
0.7652	Intermediate Similarity	NPC203486
0.7652	Intermediate Similarity	NPC329282
0.7647	Intermediate Similarity	NPC280789
0.7615	Intermediate Similarity	NPC475138
0.7615	Intermediate Similarity	NPC220596
0.7615	Intermediate Similarity	NPC82712
0.7603	Intermediate Similarity	NPC217111
0.7589	Intermediate Similarity	NPC324602
0.7586	Intermediate Similarity	NPC471133
0.7578	Intermediate Similarity	NPC470816
0.7578	Intermediate Similarity	NPC100402
0.7578	Intermediate Similarity	NPC9180
0.7565	Intermediate Similarity	NPC247976
0.7559	Intermediate Similarity	NPC318067
0.7559	Intermediate Similarity	NPC140118
0.7559	Intermediate Similarity	NPC307139
0.7559	Intermediate Similarity	NPC12881
0.7557	Intermediate Similarity	NPC72915
0.7545	Intermediate Similarity	NPC152897
0.7545	Intermediate Similarity	NPC66429
0.7544	Intermediate Similarity	NPC469481
0.7542	Intermediate Similarity	NPC475006
0.7538	Intermediate Similarity	NPC225103
0.7523	Intermediate Similarity	NPC46281
0.7521	Intermediate Similarity	NPC100767
0.752	Intermediate Similarity	NPC470585
0.752	Intermediate Similarity	NPC472679
0.752	Intermediate Similarity	NPC472680
0.7519	Intermediate Similarity	NPC126516
0.7519	Intermediate Similarity	NPC253681
0.7519	Intermediate Similarity	NPC4242
0.7519	Intermediate Similarity	NPC5486
0.7519	Intermediate Similarity	NPC471911
0.7519	Intermediate Similarity	NPC329913
0.75	Intermediate Similarity	NPC472697
0.75	Intermediate Similarity	NPC472698
0.75	Intermediate Similarity	NPC318173
0.75	Intermediate Similarity	NPC19136
0.7482	Intermediate Similarity	NPC471162
0.7481	Intermediate Similarity	NPC473443
0.7481	Intermediate Similarity	NPC49272
0.7481	Intermediate Similarity	NPC472388
0.748	Intermediate Similarity	NPC472862
0.746	Intermediate Similarity	NPC476234
0.7456	Intermediate Similarity	NPC7435
0.7455	Intermediate Similarity	NPC187725
0.7455	Intermediate Similarity	NPC154101
0.7455	Intermediate Similarity	NPC141607
0.7455	Intermediate Similarity	NPC86987
0.7438	Intermediate Similarity	NPC477475
0.7438	Intermediate Similarity	NPC469547
0.7438	Intermediate Similarity	NPC477476
0.7436	Intermediate Similarity	NPC474307
0.7434	Intermediate Similarity	NPC477767
0.7431	Intermediate Similarity	NPC298115
0.7422	Intermediate Similarity	NPC85511
0.7422	Intermediate Similarity	NPC472681
0.7422	Intermediate Similarity	NPC8990
0.7417	Intermediate Similarity	NPC133308
0.7414	Intermediate Similarity	NPC329556
0.7411	Intermediate Similarity	NPC172925
0.7411	Intermediate Similarity	NPC263347
0.7402	Intermediate Similarity	NPC269923
0.7402	Intermediate Similarity	NPC167323
0.7391	Intermediate Similarity	NPC289117
0.7391	Intermediate Similarity	NPC63737
0.7388	Intermediate Similarity	NPC477368
0.7388	Intermediate Similarity	NPC48929
0.7385	Intermediate Similarity	NPC470648
0.7385	Intermediate Similarity	NPC169913
0.7373	Intermediate Similarity	NPC474111
0.7373	Intermediate Similarity	NPC25385
0.7373	Intermediate Similarity	NPC193640
0.7373	Intermediate Similarity	NPC329705
0.7373	Intermediate Similarity	NPC475905
0.7368	Intermediate Similarity	NPC80599
0.7368	Intermediate Similarity	NPC329387
0.7368	Intermediate Similarity	NPC317280
0.7364	Intermediate Similarity	NPC274455
0.7364	Intermediate Similarity	NPC477369
0.7364	Intermediate Similarity	NPC86670
0.7364	Intermediate Similarity	NPC70940
0.7355	Intermediate Similarity	NPC218855
0.7353	Intermediate Similarity	NPC243893
0.7353	Intermediate Similarity	NPC262324
0.735	Intermediate Similarity	NPC315794
0.7348	Intermediate Similarity	NPC272946
0.7345	Intermediate Similarity	NPC155676
0.7344	Intermediate Similarity	NPC108286
0.7339	Intermediate Similarity	NPC48866
0.7339	Intermediate Similarity	NPC247406
0.7333	Intermediate Similarity	NPC232888
0.7333	Intermediate Similarity	NPC471864
0.7333	Intermediate Similarity	NPC477367
0.7328	Intermediate Similarity	NPC30491
0.7328	Intermediate Similarity	NPC262936
0.7328	Intermediate Similarity	NPC472678
0.7323	Intermediate Similarity	NPC472981
0.7319	Intermediate Similarity	NPC471862
0.7317	Intermediate Similarity	NPC274839
0.7317	Intermediate Similarity	NPC476357
0.7313	Intermediate Similarity	NPC477364
0.7308	Intermediate Similarity	NPC275576
0.7308	Intermediate Similarity	NPC470649
0.7308	Intermediate Similarity	NPC478107
0.7302	Intermediate Similarity	NPC258366
0.7302	Intermediate Similarity	NPC79933
0.7302	Intermediate Similarity	NPC473974
0.7302	Intermediate Similarity	NPC31296
0.7299	Intermediate Similarity	NPC156393
0.7297	Intermediate Similarity	NPC125226
0.7295	Intermediate Similarity	NPC143768
0.7287	Intermediate Similarity	NPC469742
0.7281	Intermediate Similarity	NPC251579
0.7281	Intermediate Similarity	NPC107243
0.7281	Intermediate Similarity	NPC133135
0.7281	Intermediate Similarity	NPC57416
0.728	Intermediate Similarity	NPC152812
0.728	Intermediate Similarity	NPC61651
0.7273	Intermediate Similarity	NPC54689
0.7265	Intermediate Similarity	NPC19856
0.7259	Intermediate Similarity	NPC477359
0.7257	Intermediate Similarity	NPC206764
0.7257	Intermediate Similarity	NPC222845
0.7257	Intermediate Similarity	NPC162001
0.7257	Intermediate Similarity	NPC45324
0.7252	Intermediate Similarity	NPC472706

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 NPC9274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	680
0.2-0.3	1573
0.3-0.4	3035
0.4-0.5	2345
0.5-0.6	1026
0.6-0.7	283
0.7-0.8	36
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
0.8348	Intermediate Similarity	NPD6858	Approved
0.8348	Intermediate Similarity	NPD7094	Approved
0.8198	Intermediate Similarity	NPD5765	Approved
0.8142	Intermediate Similarity	NPD6685	Approved
0.7876	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD7961	Discontinued
0.7727	Intermediate Similarity	NPD1693	Approved
0.7647	Intermediate Similarity	NPD6912	Phase 3
0.7642	Intermediate Similarity	NPD7009	Phase 2
0.7636	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2066	Phase 3
0.7561	Intermediate Similarity	NPD7610	Discontinued
0.7545	Intermediate Similarity	NPD1088	Approved
0.7519	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6085	Phase 2
0.75	Intermediate Similarity	NPD6663	Approved
0.7481	Intermediate Similarity	NPD7305	Phase 1
0.7462	Intermediate Similarity	NPD5736	Approved
0.746	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6065	Approved
0.7414	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1930	Approved
0.7414	Intermediate Similarity	NPD6647	Phase 2
0.7414	Intermediate Similarity	NPD1929	Approved
0.7411	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD5618	Discontinued
0.7364	Intermediate Similarity	NPD1089	Approved
0.7364	Intermediate Similarity	NPD1086	Approved
0.7364	Intermediate Similarity	NPD1090	Approved
0.7357	Intermediate Similarity	NPD7236	Approved
0.7328	Intermediate Similarity	NPD1932	Approved
0.7328	Intermediate Similarity	NPD7084	Phase 3
0.7317	Intermediate Similarity	NPD5951	Approved
0.7317	Intermediate Similarity	NPD2629	Approved
0.7273	Intermediate Similarity	NPD5346	Phase 2
0.7273	Intermediate Similarity	NPD800	Approved
0.7273	Intermediate Similarity	NPD5347	Phase 2
0.7258	Intermediate Similarity	NPD3317	Approved
0.7252	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2329	Discontinued
0.7222	Intermediate Similarity	NPD7239	Suspended
0.7193	Intermediate Similarity	NPD1989	Approved
0.7143	Intermediate Similarity	NPD1239	Approved
0.713	Intermediate Similarity	NPD1566	Phase 3
0.713	Intermediate Similarity	NPD1565	Approved
0.713	Intermediate Similarity	NPD3495	Discontinued
0.713	Intermediate Similarity	NPD1564	Approved
0.7109	Intermediate Similarity	NPD2932	Approved
0.7109	Intermediate Similarity	NPD3019	Approved
0.7109	Intermediate Similarity	NPD4199	Phase 3
0.7107	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6049	Phase 2
0.7105	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6010	Discontinued
0.7091	Intermediate Similarity	NPD4793	Discontinued
0.7091	Intermediate Similarity	NPD1087	Approved
0.709	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4479	Discontinued
0.7054	Intermediate Similarity	NPD3672	Approved
0.7054	Intermediate Similarity	NPD3673	Approved
0.704	Intermediate Similarity	NPD4766	Approved
0.7009	Intermediate Similarity	NPD226	Approved
0.7009	Intermediate Similarity	NPD7798	Approved
0.7	Intermediate Similarity	NPD5048	Discontinued
0.6991	Remote Similarity	NPD5281	Approved
0.6991	Remote Similarity	NPD5284	Approved
0.6977	Remote Similarity	NPD3095	Discontinued
0.6977	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7008	Discontinued
0.6953	Remote Similarity	NPD3091	Approved
0.6953	Remote Similarity	NPD7741	Discontinued
0.693	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD3026	Approved
0.6912	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1317	Discontinued
0.6899	Remote Similarity	NPD3024	Approved
0.6899	Remote Similarity	NPD3025	Approved
0.6899	Remote Similarity	NPD5981	Approved
0.6889	Remote Similarity	NPD7055	Discontinued
0.687	Remote Similarity	NPD1563	Approved
0.6861	Remote Similarity	NPD7715	Approved
0.6861	Remote Similarity	NPD7714	Approved
0.6812	Remote Similarity	NPD4140	Approved
0.6806	Remote Similarity	NPD7295	Approved
0.6791	Remote Similarity	NPD3094	Phase 2
0.6783	Remote Similarity	NPD7631	Approved
0.6777	Remote Similarity	NPD5909	Discontinued
0.6742	Remote Similarity	NPD3092	Approved
0.6735	Remote Similarity	NPD6273	Approved
0.6729	Remote Similarity	NPD225	Approved
0.6729	Remote Similarity	NPD227	Approved
0.6727	Remote Similarity	NPD9491	Approved
0.672	Remote Similarity	NPD3642	Approved
0.672	Remote Similarity	NPD3644	Approved
0.672	Remote Similarity	NPD3643	Approved
0.672	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4198	Discontinued
0.6696	Remote Similarity	NPD7609	Phase 3
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6693	Remote Similarity	NPD2652	Approved
0.6693	Remote Similarity	NPD2650	Approved
0.6692	Remote Similarity	NPD3798	Phase 3
0.669	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3797	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD3666	Approved
0.6643	Remote Similarity	NPD6004	Phase 3
0.6643	Remote Similarity	NPD5763	Approved
0.6643	Remote Similarity	NPD5762	Approved
0.6643	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6005	Phase 3
0.6643	Remote Similarity	NPD6002	Phase 3
0.6643	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.664	Remote Similarity	NPD2067	Discontinued
0.6639	Remote Similarity	NPD9495	Approved
0.6638	Remote Similarity	NPD1508	Approved
0.6619	Remote Similarity	NPD8032	Phase 2
0.6613	Remote Similarity	NPD6899	Approved
0.6613	Remote Similarity	NPD6881	Approved
0.6613	Remote Similarity	NPD6406	Approved
0.661	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1283	Approved
0.6591	Remote Similarity	NPD5125	Phase 3
0.6591	Remote Similarity	NPD5126	Approved
0.6587	Remote Similarity	NPD6649	Approved
0.6587	Remote Similarity	NPD6650	Approved
0.6585	Remote Similarity	NPD7128	Approved
0.6585	Remote Similarity	NPD6675	Approved
0.6585	Remote Similarity	NPD6402	Approved
0.6585	Remote Similarity	NPD5739	Approved
0.6573	Remote Similarity	NPD7137	Phase 2
0.6571	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3598	Phase 3
0.656	Remote Similarity	NPD6372	Approved
0.656	Remote Similarity	NPD2182	Approved
0.656	Remote Similarity	NPD6373	Approved
0.6549	Remote Similarity	NPD5330	Approved
0.6549	Remote Similarity	NPD7334	Approved
0.6549	Remote Similarity	NPD7521	Approved
0.6549	Remote Similarity	NPD6409	Approved
0.6549	Remote Similarity	NPD6684	Approved
0.6549	Remote Similarity	NPD7146	Approved
0.6532	Remote Similarity	NPD5697	Approved
0.6529	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4629	Approved
0.6525	Remote Similarity	NPD5210	Approved
0.6522	Remote Similarity	NPD4753	Phase 2
0.6508	Remote Similarity	NPD4234	Approved
0.6508	Remote Similarity	NPD4233	Approved
0.6508	Remote Similarity	NPD7102	Approved
0.6508	Remote Similarity	NPD7290	Approved
0.6508	Remote Similarity	NPD6883	Approved
0.6504	Remote Similarity	NPD1237	Approved
0.65	Remote Similarity	NPD5696	Approved
0.65	Remote Similarity	NPD7799	Discontinued
0.6496	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD5647	Approved
0.6493	Remote Similarity	NPD3132	Approved
0.6493	Remote Similarity	NPD3131	Approved
0.6493	Remote Similarity	NPD4215	Approved
0.6493	Remote Similarity	NPD2612	Approved
0.6493	Remote Similarity	NPD2608	Approved
0.6493	Remote Similarity	NPD4216	Approved
0.6493	Remote Similarity	NPD4218	Approved
0.6493	Remote Similarity	NPD2610	Approved
0.6493	Remote Similarity	NPD4217	Approved
0.6493	Remote Similarity	NPD2609	Approved
0.6493	Remote Similarity	NPD2611	Approved
0.6486	Remote Similarity	NPD3667	Approved
0.648	Remote Similarity	NPD7320	Approved
0.648	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD1843	Approved
0.6467	Remote Similarity	NPD7606	Phase 3
0.6466	Remote Similarity	NPD2345	Approved
0.6466	Remote Similarity	NPD4059	Approved
0.6457	Remote Similarity	NPD8130	Phase 1
0.6457	Remote Similarity	NPD6869	Approved
0.6457	Remote Similarity	NPD6617	Approved
0.6457	Remote Similarity	NPD6847	Approved
0.6454	Remote Similarity	NPD2979	Phase 3
0.6446	Remote Similarity	NPD5285	Approved
0.6446	Remote Similarity	NPD5286	Approved
0.6446	Remote Similarity	NPD4696	Approved
0.6444	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7082	Approved
0.6435	Remote Similarity	NPD6903	Approved
0.6435	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7077	Approved
0.6434	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7076	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