NPASS Compound

Structure

NPC274089 OpenBabel07101718312D 32 34 0 0 1 0 0 0 0 0999 V2000 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 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 -1.6092 -0.1691 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 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 2 6 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 6 17 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 29 1 0 0 0 0 23 12 1 1 0 0 0 23 25 1 0 0 0 0 24 13 1 1 0 0 0 24 26 1 0 0 0 0 25 14 1 6 0 0 0 25 26 1 0 0 0 0 26 15 1 6 0 0 0 27 29 2 3 0 0 0 27 30 1 0 0 0 0 28 31 2 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	433.26
Volume:	480.814
LogP:	4.545
LogD:	3.793
LogS:	-3.771
# Rotatable Bonds:	12
TPSA:	66.4
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	4.08
Fsp3:	0.429
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:	-5.291
MDCK Permeability:	1.2876588698418345e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.638
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	100.12212371826172%
Volume Distribution (VD):	0.29
Pgp-substrate:	0.9976459741592407%

ADMET: Metabolism

CYP1A2-inhibitor:	0.149
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.838
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.779
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	1.077
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.201
Human Hepatotoxicity (H-HT):	0.753
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.91
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.868

Download Data

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

Natural Product: NPC274089

Natural Product ID:	NPC274089
*Common Name:**	Aplidic Acid C
IUPAC Name:	(E)-6-[(3aR,4R,5R,7aS)-4-[(1E,3E)-5-oxo-5-(2-phenylethylamino)penta-1,3-dienyl]-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hex-5-enoic acid
Synonyms:	Aplidic Acid C
Standard InCHIKey:	FAGHADWDEDDYSS-ZFTNNBPWSA-N
Standard InCHI:	InChI=1S/C28H35NO3/c30-27(29-21-20-22-10-3-1-4-11-22)16-8-7-14-25-23(12-5-2-6-17-28(31)32)18-19-24-13-9-15-26(24)25/h1,3-5,7-8,10-12,14,16,18-19,23-26H,2,6,9,13,15,17,20-21H2,(H,29,30)(H,31,32)/b12-5+,14-7+,16-8+/t23-,24+,25+,26-/m1/s1
SMILES:	c1ccc(cc1)CCN=C(/C=C/C=C/[C@H]1[C@H](/C=C/CCCC(=O)O)C=C[C@@H]2CCC[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079214
PubChem CID:	46882294
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0003086] Medium-chain fatty acids

*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
NPO33298	polyclinidae	Family	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783438]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	12.3	ug ml-1	PMID[551063]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	14.7	ug ml-1	PMID[551063]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	14.5	ug ml-1	PMID[551063]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	14.0	ug ml-1	PMID[551063]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	12.0	ug ml-1	PMID[551063]

☑ 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 NPC274089 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	109
0.1-0.2	726
0.2-0.3	2829
0.3-0.4	13557
0.4-0.5	20372
0.5-0.6	4344
0.6-0.7	663
0.7-0.8	94
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC191215
0.8911	High Similarity	NPC469457
0.78	Intermediate Similarity	NPC203076
0.7797	Intermediate Similarity	NPC80150
0.7757	Intermediate Similarity	NPC12730
0.7658	Intermediate Similarity	NPC327481
0.7647	Intermediate Similarity	NPC190663
0.7576	Intermediate Similarity	NPC14326
0.7565	Intermediate Similarity	NPC474584
0.7549	Intermediate Similarity	NPC473031
0.7545	Intermediate Similarity	NPC471317
0.7545	Intermediate Similarity	NPC164859
0.7545	Intermediate Similarity	NPC202613
0.7544	Intermediate Similarity	NPC319579
0.7521	Intermediate Similarity	NPC160493
0.7476	Intermediate Similarity	NPC325441
0.7407	Intermediate Similarity	NPC251579
0.7407	Intermediate Similarity	NPC133135
0.7381	Intermediate Similarity	NPC478147
0.7379	Intermediate Similarity	NPC471638
0.7353	Intermediate Similarity	NPC3210
0.7345	Intermediate Similarity	NPC45033
0.7339	Intermediate Similarity	NPC120393
0.7333	Intermediate Similarity	NPC78041
0.7333	Intermediate Similarity	NPC121872
0.7333	Intermediate Similarity	NPC258627
0.7333	Intermediate Similarity	NPC209764
0.7333	Intermediate Similarity	NPC310467
0.7333	Intermediate Similarity	NPC141139
0.7333	Intermediate Similarity	NPC471307
0.7333	Intermediate Similarity	NPC159178
0.7333	Intermediate Similarity	NPC74936
0.7317	Intermediate Similarity	NPC472415
0.7315	Intermediate Similarity	NPC3371
0.7315	Intermediate Similarity	NPC25565
0.7302	Intermediate Similarity	NPC296712
0.7297	Intermediate Similarity	NPC318154
0.7266	Intermediate Similarity	NPC246913
0.7265	Intermediate Similarity	NPC273814
0.725	Intermediate Similarity	NPC169328
0.7248	Intermediate Similarity	NPC469892
0.7248	Intermediate Similarity	NPC473501
0.7248	Intermediate Similarity	NPC33168
0.7248	Intermediate Similarity	NPC469890
0.7248	Intermediate Similarity	NPC475439
0.7248	Intermediate Similarity	NPC469891
0.7238	Intermediate Similarity	NPC470877
0.7236	Intermediate Similarity	NPC474862
0.7222	Intermediate Similarity	NPC303045
0.7222	Intermediate Similarity	NPC161972
0.7222	Intermediate Similarity	NPC58674
0.7213	Intermediate Similarity	NPC478015
0.7213	Intermediate Similarity	NPC478014
0.7213	Intermediate Similarity	NPC478016
0.7207	Intermediate Similarity	NPC264728
0.72	Intermediate Similarity	NPC472414
0.72	Intermediate Similarity	NPC4974
0.719	Intermediate Similarity	NPC237420
0.7179	Intermediate Similarity	NPC329011
0.717	Intermediate Similarity	NPC172128
0.717	Intermediate Similarity	NPC316108
0.7165	Intermediate Similarity	NPC116057
0.7165	Intermediate Similarity	NPC472413
0.7157	Intermediate Similarity	NPC44830
0.7156	Intermediate Similarity	NPC469893
0.7143	Intermediate Similarity	NPC12429
0.713	Intermediate Similarity	NPC471309
0.713	Intermediate Similarity	NPC142297
0.7105	Intermediate Similarity	NPC211551
0.7103	Intermediate Similarity	NPC226438
0.7103	Intermediate Similarity	NPC245259
0.7094	Intermediate Similarity	NPC474149
0.7091	Intermediate Similarity	NPC293628
0.7091	Intermediate Similarity	NPC10781
0.7091	Intermediate Similarity	NPC122493
0.7091	Intermediate Similarity	NPC311242
0.7069	Intermediate Similarity	NPC96224
0.7069	Intermediate Similarity	NPC24101
0.7049	Intermediate Similarity	NPC314992
0.7043	Intermediate Similarity	NPC244933
0.7043	Intermediate Similarity	NPC85560
0.7037	Intermediate Similarity	NPC323164
0.7037	Intermediate Similarity	NPC475057
0.7031	Intermediate Similarity	NPC71271
0.7	Intermediate Similarity	NPC33742
0.7	Intermediate Similarity	NPC326966
0.6992	Remote Similarity	NPC319950
0.6975	Remote Similarity	NPC242957
0.6975	Remote Similarity	NPC306977
0.6975	Remote Similarity	NPC206414
0.6975	Remote Similarity	NPC287055
0.6967	Remote Similarity	NPC470545
0.6964	Remote Similarity	NPC7435
0.6957	Remote Similarity	NPC321670
0.6953	Remote Similarity	NPC210950
0.6953	Remote Similarity	NPC199738
0.6949	Remote Similarity	NPC323007
0.6944	Remote Similarity	NPC475059
0.6944	Remote Similarity	NPC475023
0.6942	Remote Similarity	NPC197470
0.6942	Remote Similarity	NPC188010
0.694	Remote Similarity	NPC153007
0.6937	Remote Similarity	NPC324569
0.6935	Remote Similarity	NPC45777
0.6935	Remote Similarity	NPC477061
0.6929	Remote Similarity	NPC47667
0.6923	Remote Similarity	NPC183722
0.6923	Remote Similarity	NPC182549
0.6923	Remote Similarity	NPC114741
0.6917	Remote Similarity	NPC276949
0.6917	Remote Similarity	NPC35850
0.6911	Remote Similarity	NPC470546
0.6905	Remote Similarity	NPC35996
0.6897	Remote Similarity	NPC231705
0.6887	Remote Similarity	NPC322387
0.6885	Remote Similarity	NPC470544
0.6885	Remote Similarity	NPC2265
0.6875	Remote Similarity	NPC477937
0.6875	Remote Similarity	NPC322598
0.687	Remote Similarity	NPC194390
0.687	Remote Similarity	NPC113326
0.687	Remote Similarity	NPC88267
0.687	Remote Similarity	NPC224610
0.6864	Remote Similarity	NPC258056
0.6863	Remote Similarity	NPC127343
0.686	Remote Similarity	NPC471318
0.6852	Remote Similarity	NPC70940
0.6852	Remote Similarity	NPC274455
0.6852	Remote Similarity	NPC86670
0.6846	Remote Similarity	NPC325651
0.6842	Remote Similarity	NPC279045
0.6842	Remote Similarity	NPC113325
0.6829	Remote Similarity	NPC471926
0.6825	Remote Similarity	NPC109151
0.6825	Remote Similarity	NPC27581
0.6818	Remote Similarity	NPC244866
0.681	Remote Similarity	NPC67043
0.6807	Remote Similarity	NPC313981
0.68	Remote Similarity	NPC200964
0.6791	Remote Similarity	NPC208725
0.6786	Remote Similarity	NPC477767
0.6783	Remote Similarity	NPC178902
0.6767	Remote Similarity	NPC90693
0.6767	Remote Similarity	NPC228511
0.6767	Remote Similarity	NPC64897
0.6765	Remote Similarity	NPC239770
0.6752	Remote Similarity	NPC471447
0.6748	Remote Similarity	NPC315276
0.6748	Remote Similarity	NPC471925
0.6748	Remote Similarity	NPC285926
0.6748	Remote Similarity	NPC471928
0.6748	Remote Similarity	NPC14672
0.6748	Remote Similarity	NPC471924
0.6746	Remote Similarity	NPC71684
0.6742	Remote Similarity	NPC42423
0.6742	Remote Similarity	NPC45191
0.6739	Remote Similarity	NPC473922
0.6729	Remote Similarity	NPC194326
0.6729	Remote Similarity	NPC198747
0.6727	Remote Similarity	NPC265521
0.6726	Remote Similarity	NPC317280
0.6726	Remote Similarity	NPC179411
0.6726	Remote Similarity	NPC329387
0.6719	Remote Similarity	NPC473938
0.6697	Remote Similarity	NPC84288
0.6697	Remote Similarity	NPC26224
0.6696	Remote Similarity	NPC261947
0.6695	Remote Similarity	NPC249811
0.6694	Remote Similarity	NPC254088
0.6693	Remote Similarity	NPC169485
0.6693	Remote Similarity	NPC291027
0.6693	Remote Similarity	NPC84281
0.6693	Remote Similarity	NPC317474
0.6693	Remote Similarity	NPC213126
0.6693	Remote Similarity	NPC142577
0.6692	Remote Similarity	NPC476353
0.6667	Remote Similarity	NPC6913
0.6667	Remote Similarity	NPC285773
0.6667	Remote Similarity	NPC474559
0.6667	Remote Similarity	NPC235421
0.6667	Remote Similarity	NPC6570
0.6667	Remote Similarity	NPC476183
0.6667	Remote Similarity	NPC317254
0.6643	Remote Similarity	NPC328824
0.6643	Remote Similarity	NPC475578
0.6641	Remote Similarity	NPC6975
0.664	Remote Similarity	NPC220698
0.6639	Remote Similarity	NPC153690
0.6638	Remote Similarity	NPC471310
0.6636	Remote Similarity	NPC86987
0.6619	Remote Similarity	NPC316008
0.6619	Remote Similarity	NPC313867
0.6615	Remote Similarity	NPC278097
0.6614	Remote Similarity	NPC476184
0.6614	Remote Similarity	NPC476281
0.6613	Remote Similarity	NPC239357
0.6609	Remote Similarity	NPC225079
0.6609	Remote Similarity	NPC133809
0.6609	Remote Similarity	NPC128248
0.6609	Remote Similarity	NPC136810

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 NPC274089 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	440
0.2-0.3	809
0.3-0.4	2303
0.4-0.5	3562
0.5-0.6	1542
0.6-0.7	377
0.7-0.8	14
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
0.8018	Intermediate Similarity	NPD3642	Approved
0.8018	Intermediate Similarity	NPD3643	Approved
0.8018	Intermediate Similarity	NPD3644	Approved
0.75	Intermediate Similarity	NPD253	Approved
0.7431	Intermediate Similarity	NPD1067	Discontinued
0.7417	Intermediate Similarity	NPD5981	Approved
0.7407	Intermediate Similarity	NPD2487	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4479	Discontinued
0.7281	Intermediate Similarity	NPD6406	Approved
0.7241	Intermediate Similarity	NPD5927	Discontinued
0.7232	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4814	Discontinued
0.7207	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3598	Phase 3
0.72	Intermediate Similarity	NPD6325	Discontinued
0.7196	Intermediate Similarity	NPD6690	Approved
0.7154	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9712	Approved
0.7107	Intermediate Similarity	NPD1758	Phase 1
0.7105	Intermediate Similarity	NPD1040	Phase 2
0.7105	Intermediate Similarity	NPD1018	Approved
0.7097	Intermediate Similarity	NPD5618	Discontinued
0.7091	Intermediate Similarity	NPD9566	Approved
0.708	Intermediate Similarity	NPD3681	Approved
0.708	Intermediate Similarity	NPD3683	Approved
0.7075	Intermediate Similarity	NPD5346	Phase 2
0.7075	Intermediate Similarity	NPD5347	Phase 2
0.7063	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2217	Approved
0.7049	Intermediate Similarity	NPD2218	Phase 2
0.7049	Intermediate Similarity	NPD1759	Phase 1
0.7048	Intermediate Similarity	NPD4793	Discontinued
0.704	Intermediate Similarity	NPD6624	Discontinued
0.7027	Intermediate Similarity	NPD9710	Approved
0.7027	Intermediate Similarity	NPD9711	Approved
0.7018	Intermediate Similarity	NPD179	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2895	Discontinued
0.6992	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4818	Approved
0.6991	Remote Similarity	NPD4817	Approved
0.6972	Remote Similarity	NPD1066	Discontinued
0.6957	Remote Similarity	NPD999	Phase 2
0.6942	Remote Similarity	NPD1348	Approved
0.693	Remote Similarity	NPD6647	Phase 2
0.693	Remote Similarity	NPD5765	Approved
0.693	Remote Similarity	NPD3680	Approved
0.693	Remote Similarity	NPD5103	Approved
0.693	Remote Similarity	NPD3682	Approved
0.6923	Remote Similarity	NPD4717	Approved
0.6923	Remote Similarity	NPD4718	Approved
0.6923	Remote Similarity	NPD4720	Approved
0.6917	Remote Similarity	NPD2650	Approved
0.6917	Remote Similarity	NPD2652	Approved
0.6911	Remote Similarity	NPD2617	Discontinued
0.6911	Remote Similarity	NPD6093	Discontinued
0.6909	Remote Similarity	NPD1693	Approved
0.6905	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3123	Discovery
0.6885	Remote Similarity	NPD5162	Approved
0.6881	Remote Similarity	NPD1814	Approved
0.6881	Remote Similarity	NPD1812	Approved
0.6875	Remote Similarity	NPD6302	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5236	Approved
0.6864	Remote Similarity	NPD5235	Approved
0.6864	Remote Similarity	NPD5240	Approved
0.6864	Remote Similarity	NPD5237	Approved
0.6864	Remote Similarity	NPD5239	Approved
0.6857	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1090	Approved
0.6852	Remote Similarity	NPD1089	Approved
0.6852	Remote Similarity	NPD1086	Approved
0.6847	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2607	Approved
0.6827	Remote Similarity	NPD3971	Phase 1
0.6825	Remote Similarity	NPD3603	Phase 3
0.6825	Remote Similarity	NPD4807	Approved
0.6825	Remote Similarity	NPD4806	Approved
0.6807	Remote Similarity	NPD2201	Approved
0.6807	Remote Similarity	NPD188	Approved
0.6807	Remote Similarity	NPD189	Phase 3
0.6807	Remote Similarity	NPD2583	Phase 2
0.68	Remote Similarity	NPD5306	Approved
0.68	Remote Similarity	NPD5305	Approved
0.6796	Remote Similarity	NPD226	Approved
0.6794	Remote Similarity	NPD3136	Phase 2
0.6783	Remote Similarity	NPD4231	Approved
0.6783	Remote Similarity	NPD4229	Approved
0.6777	Remote Similarity	NPD1682	Approved
0.6777	Remote Similarity	NPD1680	Approved
0.6777	Remote Similarity	NPD1681	Approved
0.6772	Remote Similarity	NPD2584	Suspended
0.6759	Remote Similarity	NPD800	Approved
0.6757	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD467	Phase 1
0.6752	Remote Similarity	NPD6685	Approved
0.6727	Remote Similarity	NPD1088	Approved
0.6724	Remote Similarity	NPD5909	Discontinued
0.672	Remote Similarity	NPD4105	Approved
0.672	Remote Similarity	NPD4102	Approved
0.672	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8643	Discontinued
0.6694	Remote Similarity	NPD181	Approved
0.6693	Remote Similarity	NPD4216	Approved
0.6693	Remote Similarity	NPD2612	Approved
0.6693	Remote Similarity	NPD2608	Approved
0.6693	Remote Similarity	NPD3131	Approved
0.6693	Remote Similarity	NPD4218	Approved
0.6693	Remote Similarity	NPD4217	Approved
0.6693	Remote Similarity	NPD4215	Approved
0.6693	Remote Similarity	NPD2610	Approved
0.6693	Remote Similarity	NPD3132	Approved
0.6693	Remote Similarity	NPD2611	Approved
0.6693	Remote Similarity	NPD2609	Approved
0.6692	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4738	Phase 2
0.6667	Remote Similarity	NPD4254	Approved
0.6667	Remote Similarity	NPD3098	Discontinued
0.6667	Remote Similarity	NPD5578	Approved
0.6667	Remote Similarity	NPD3125	Approved
0.6667	Remote Similarity	NPD1101	Approved
0.6667	Remote Similarity	NPD4253	Approved
0.6667	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2066	Phase 3
0.6667	Remote Similarity	NPD9491	Approved
0.6667	Remote Similarity	NPD5367	Discontinued
0.6642	Remote Similarity	NPD6346	Approved
0.6642	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3661	Approved
0.6641	Remote Similarity	NPD3663	Approved
0.6641	Remote Similarity	NPD7828	Discontinued
0.6641	Remote Similarity	NPD3664	Approved
0.6641	Remote Similarity	NPD3662	Phase 3
0.6639	Remote Similarity	NPD1374	Approved
0.6639	Remote Similarity	NPD1370	Approved
0.6639	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1373	Approved
0.6639	Remote Similarity	NPD1371	Approved
0.6638	Remote Similarity	NPD4656	Approved
0.6638	Remote Similarity	NPD4658	Approved
0.6636	Remote Similarity	NPD1239	Approved
0.6636	Remote Similarity	NPD530	Approved
0.6614	Remote Similarity	NPD4136	Approved
0.6614	Remote Similarity	NPD4135	Approved
0.6614	Remote Similarity	NPD4106	Approved
0.6613	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6912	Phase 3
0.6612	Remote Similarity	NPD9508	Approved
0.6607	Remote Similarity	NPD6049	Phase 2
0.6607	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4094	Approved
0.6591	Remote Similarity	NPD4125	Approved
0.6587	Remote Similarity	NPD6993	Approved
0.6587	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6994	Approved
0.6585	Remote Similarity	NPD747	Discontinued
0.6585	Remote Similarity	NPD4766	Approved
0.6583	Remote Similarity	NPD1752	Approved
0.6583	Remote Similarity	NPD4233	Approved
0.6583	Remote Similarity	NPD1756	Approved
0.6583	Remote Similarity	NPD4234	Approved
0.6579	Remote Similarity	NPD5926	Approved
0.6577	Remote Similarity	NPD752	Approved
0.6574	Remote Similarity	NPD1087	Approved
0.6574	Remote Similarity	NPD187	Approved
0.6567	Remote Similarity	NPD7715	Approved
0.6567	Remote Similarity	NPD7714	Approved
0.6565	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4480	Approved
0.656	Remote Similarity	NPD2115	Approved
0.656	Remote Similarity	NPD2116	Approved
0.656	Remote Similarity	NPD2117	Pre-registration
0.6557	Remote Similarity	NPD3066	Phase 2
0.6557	Remote Similarity	NPD4165	Phase 2
0.6555	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4119	Approved
0.6552	Remote Similarity	NPD4803	Discontinued
0.6545	Remote Similarity	NPD3672	Approved
0.6545	Remote Similarity	NPD3673	Approved
0.6535	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD9716	Approved
0.6525	Remote Similarity	NPD7740	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5717	Approved
0.6525	Remote Similarity	NPD5048	Discontinued
0.6519	Remote Similarity	NPD8416	Discontinued
0.6518	Remote Similarity	NPD720	Approved
0.6518	Remote Similarity	NPD719	Approved
0.6518	Remote Similarity	NPD1080	Approved
0.6515	Remote Similarity	NPD5759	Approved
0.6515	Remote Similarity	NPD5204	Approved
0.6508	Remote Similarity	NPD2994	Approved
0.6505	Remote Similarity	NPD227	Approved
0.6505	Remote Similarity	NPD225	Approved
0.6504	Remote Similarity	NPD2228	Approved
0.6504	Remote Similarity	NPD23	Approved
0.6504	Remote Similarity	NPD2234	Approved
0.6504	Remote Similarity	NPD2229	Approved
0.6496	Remote Similarity	NPD1542	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