NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	280.721
LogP:	3.246
LogD:	3.552
LogS:	-3.752
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	4.376
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.647
MDCK Permeability:	3.0231101845856756e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.917
Plasma Protein Binding (PPB):	53.55464553833008%
Volume Distribution (VD):	0.81
Pgp-substrate:	50.62103271484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.537
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.47
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	5.519
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.51
Carcinogencity:	0.116
Eye Corrosion:	0.195
Eye Irritation:	0.775
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC475951

Natural Product ID:	NPC475951
*Common Name:**	Beta-Cyclocostunolide
IUPAC Name:	(3R,3aS,5aR,9aS,9bS)-3-(methoxymethyl)-5a-methyl-9-methylidene-3a,4,5,6,7,8,9a,9b-octahydro-3H-benzo[g][1]benzofuran-2-one
Synonyms:	Beta-Cyclocostunolide
Standard InCHIKey:	OCZYALGLUPTEFV-JHZZJYKESA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-10-5-4-7-16(2)8-6-11-12(9-18-3)15(17)19-14(11)13(10)16/h11-14H,1,4-9H2,2-3H3/t11-,12-,13+,14-,16+/m0/s1
SMILES:	CC12CCCC(=C)C1C3C(CC2)C(C(=O)O3)COC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519452
PubChem CID:	44568209
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:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[18409040]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[18579374]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25068579]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	root	n.a.	PMID[8541643]
NPO30603	Saussurea lappa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	109.81	ug.mL-1	PMID[503765]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	88.49	ug.mL-1	PMID[503765]

☑ 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 NPC475951 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	184
0.1-0.2	1604
0.2-0.3	6390
0.3-0.4	14791
0.4-0.5	6967
0.5-0.6	6010
0.6-0.7	5533
0.7-0.8	1153
0.8-0.85	53
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC92489
0.8987	High Similarity	NPC209318
0.8987	High Similarity	NPC223330
0.8642	High Similarity	NPC226988
0.8588	High Similarity	NPC253618
0.8588	High Similarity	NPC77001
0.8488	Intermediate Similarity	NPC475776
0.8452	Intermediate Similarity	NPC85698
0.8452	Intermediate Similarity	NPC9231
0.8442	Intermediate Similarity	NPC474755
0.8434	Intermediate Similarity	NPC97505
0.8434	Intermediate Similarity	NPC139566
0.8395	Intermediate Similarity	NPC274522
0.8395	Intermediate Similarity	NPC476265
0.8372	Intermediate Similarity	NPC194642
0.8353	Intermediate Similarity	NPC305029
0.8353	Intermediate Similarity	NPC175293
0.8293	Intermediate Similarity	NPC38642
0.8256	Intermediate Similarity	NPC477128
0.8235	Intermediate Similarity	NPC185638
0.8235	Intermediate Similarity	NPC6979
0.8214	Intermediate Similarity	NPC219011
0.8214	Intermediate Similarity	NPC470011
0.8171	Intermediate Similarity	NPC170038
0.8148	Intermediate Similarity	NPC35574
0.814	Intermediate Similarity	NPC181103
0.8125	Intermediate Similarity	NPC474316
0.8125	Intermediate Similarity	NPC476601
0.8125	Intermediate Similarity	NPC475744
0.8125	Intermediate Similarity	NPC476985
0.8118	Intermediate Similarity	NPC329738
0.8111	Intermediate Similarity	NPC210214
0.8111	Intermediate Similarity	NPC157686
0.8111	Intermediate Similarity	NPC259042
0.8095	Intermediate Similarity	NPC194637
0.8095	Intermediate Similarity	NPC471037
0.8072	Intermediate Similarity	NPC475665
0.8049	Intermediate Similarity	NPC474754
0.8049	Intermediate Similarity	NPC118987
0.8046	Intermediate Similarity	NPC474845
0.8043	Intermediate Similarity	NPC164349
0.8026	Intermediate Similarity	NPC469868
0.8025	Intermediate Similarity	NPC474433
0.8023	Intermediate Similarity	NPC471042
0.8022	Intermediate Similarity	NPC13949
0.8022	Intermediate Similarity	NPC473964
0.8	Intermediate Similarity	NPC474841
0.8	Intermediate Similarity	NPC473434
0.8	Intermediate Similarity	NPC475509
0.8	Intermediate Similarity	NPC148000
0.8	Intermediate Similarity	NPC225474
0.8	Intermediate Similarity	NPC469596
0.8	Intermediate Similarity	NPC24861
0.8	Intermediate Similarity	NPC471446
0.7978	Intermediate Similarity	NPC250753
0.7978	Intermediate Similarity	NPC49420
0.7978	Intermediate Similarity	NPC475416
0.7978	Intermediate Similarity	NPC471901
0.7976	Intermediate Similarity	NPC476458
0.7976	Intermediate Similarity	NPC258153
0.7976	Intermediate Similarity	NPC476292
0.7976	Intermediate Similarity	NPC474605
0.7975	Intermediate Similarity	NPC109510
0.7957	Intermediate Similarity	NPC477655
0.7957	Intermediate Similarity	NPC477656
0.7955	Intermediate Similarity	NPC471222
0.7955	Intermediate Similarity	NPC116620
0.7955	Intermediate Similarity	NPC11611
0.7955	Intermediate Similarity	NPC471043
0.7935	Intermediate Similarity	NPC474921
0.7935	Intermediate Similarity	NPC253586
0.7935	Intermediate Similarity	NPC473963
0.7931	Intermediate Similarity	NPC470012
0.7912	Intermediate Similarity	NPC205173
0.7912	Intermediate Similarity	NPC56369
0.7907	Intermediate Similarity	NPC98270
0.7907	Intermediate Similarity	NPC476602
0.7901	Intermediate Similarity	NPC41017
0.7889	Intermediate Similarity	NPC287118
0.7889	Intermediate Similarity	NPC473690
0.7889	Intermediate Similarity	NPC471902
0.7889	Intermediate Similarity	NPC147272
0.7882	Intermediate Similarity	NPC470948
0.7872	Intermediate Similarity	NPC39683
0.7865	Intermediate Similarity	NPC8062
0.7865	Intermediate Similarity	NPC153853
0.7849	Intermediate Similarity	NPC78427
0.7849	Intermediate Similarity	NPC16911
0.7841	Intermediate Similarity	NPC215831
0.7841	Intermediate Similarity	NPC146937
0.7841	Intermediate Similarity	NPC80335
0.7841	Intermediate Similarity	NPC471900
0.7831	Intermediate Similarity	NPC471475
0.7826	Intermediate Similarity	NPC93245
0.7826	Intermediate Similarity	NPC256227
0.7816	Intermediate Similarity	NPC477920
0.7805	Intermediate Similarity	NPC469867
0.7805	Intermediate Similarity	NPC238227
0.7802	Intermediate Similarity	NPC470697
0.7802	Intermediate Similarity	NPC473431
0.7802	Intermediate Similarity	NPC477130
0.7802	Intermediate Similarity	NPC477129
0.7802	Intermediate Similarity	NPC473280
0.7802	Intermediate Similarity	NPC471078
0.7802	Intermediate Similarity	NPC473435
0.7791	Intermediate Similarity	NPC469407
0.7791	Intermediate Similarity	NPC100391
0.7789	Intermediate Similarity	NPC164551
0.7778	Intermediate Similarity	NPC160506
0.7778	Intermediate Similarity	NPC233345
0.7778	Intermediate Similarity	NPC476934
0.7778	Intermediate Similarity	NPC186363
0.7778	Intermediate Similarity	NPC470230
0.7766	Intermediate Similarity	NPC287676
0.7766	Intermediate Similarity	NPC267921
0.7766	Intermediate Similarity	NPC47024
0.7766	Intermediate Similarity	NPC108371
0.7765	Intermediate Similarity	NPC476984
0.7765	Intermediate Similarity	NPC110780
0.7765	Intermediate Similarity	NPC475395
0.7765	Intermediate Similarity	NPC476935
0.7763	Intermediate Similarity	NPC474768
0.7753	Intermediate Similarity	NPC213832
0.7753	Intermediate Similarity	NPC471342
0.7753	Intermediate Similarity	NPC57954
0.7753	Intermediate Similarity	NPC73995
0.7753	Intermediate Similarity	NPC469866
0.775	Intermediate Similarity	NPC279241
0.7742	Intermediate Similarity	NPC469810
0.7742	Intermediate Similarity	NPC136781
0.7742	Intermediate Similarity	NPC96839
0.7738	Intermediate Similarity	NPC195424
0.7727	Intermediate Similarity	NPC134197
0.7727	Intermediate Similarity	NPC165895
0.7717	Intermediate Similarity	NPC90014
0.7717	Intermediate Similarity	NPC195715
0.7711	Intermediate Similarity	NPC476986
0.7711	Intermediate Similarity	NPC470905
0.7708	Intermediate Similarity	NPC87927
0.7708	Intermediate Similarity	NPC99510
0.7701	Intermediate Similarity	NPC52628
0.7701	Intermediate Similarity	NPC102292
0.7701	Intermediate Similarity	NPC470223
0.7692	Intermediate Similarity	NPC294263
0.7692	Intermediate Similarity	NPC63118
0.7692	Intermediate Similarity	NPC474185
0.7692	Intermediate Similarity	NPC470224
0.7692	Intermediate Similarity	NPC474436
0.7692	Intermediate Similarity	NPC49776
0.7692	Intermediate Similarity	NPC199543
0.7684	Intermediate Similarity	NPC148279
0.7684	Intermediate Similarity	NPC308824
0.7684	Intermediate Similarity	NPC46848
0.7684	Intermediate Similarity	NPC289148
0.7684	Intermediate Similarity	NPC52899
0.7684	Intermediate Similarity	NPC163963
0.7684	Intermediate Similarity	NPC242666
0.7674	Intermediate Similarity	NPC170862
0.7667	Intermediate Similarity	NPC161638
0.7667	Intermediate Similarity	NPC152467
0.7662	Intermediate Similarity	NPC84562
0.766	Intermediate Similarity	NPC474793
0.766	Intermediate Similarity	NPC469986
0.766	Intermediate Similarity	NPC471038
0.766	Intermediate Similarity	NPC26270
0.766	Intermediate Similarity	NPC476806
0.766	Intermediate Similarity	NPC476807
0.7654	Intermediate Similarity	NPC55508
0.7653	Intermediate Similarity	NPC284732
0.7653	Intermediate Similarity	NPC78966
0.7647	Intermediate Similarity	NPC232625
0.7647	Intermediate Similarity	NPC473420
0.7647	Intermediate Similarity	NPC476988
0.764	Intermediate Similarity	NPC56413
0.764	Intermediate Similarity	NPC28227
0.764	Intermediate Similarity	NPC4309
0.764	Intermediate Similarity	NPC277771
0.7634	Intermediate Similarity	NPC120708
0.7634	Intermediate Similarity	NPC106425
0.7634	Intermediate Similarity	NPC132824
0.7634	Intermediate Similarity	NPC284518
0.7634	Intermediate Similarity	NPC327788
0.7634	Intermediate Similarity	NPC307164
0.7634	Intermediate Similarity	NPC151725
0.7634	Intermediate Similarity	NPC122324
0.7619	Intermediate Similarity	NPC263951
0.7614	Intermediate Similarity	NPC91525
0.7614	Intermediate Similarity	NPC12774
0.7614	Intermediate Similarity	NPC329943
0.7614	Intermediate Similarity	NPC9892
0.7614	Intermediate Similarity	NPC10005
0.7614	Intermediate Similarity	NPC264127
0.7614	Intermediate Similarity	NPC325594
0.7614	Intermediate Similarity	NPC250981
0.7609	Intermediate Similarity	NPC78580
0.7609	Intermediate Similarity	NPC184006
0.7609	Intermediate Similarity	NPC84893
0.7609	Intermediate Similarity	NPC47853
0.7609	Intermediate Similarity	NPC303863
0.7609	Intermediate Similarity	NPC23621

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 NPC475951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	2057
0.2-0.3	4056
0.3-0.4	1907
0.4-0.5	509
0.5-0.6	209
0.6-0.7	196
0.7-0.8	40
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
0.7778	Intermediate Similarity	NPD8035	Phase 2
0.7778	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7900	Approved
0.7416	Intermediate Similarity	NPD6684	Approved
0.7416	Intermediate Similarity	NPD7334	Approved
0.7416	Intermediate Similarity	NPD7521	Approved
0.7416	Intermediate Similarity	NPD7146	Approved
0.7416	Intermediate Similarity	NPD6409	Approved
0.7416	Intermediate Similarity	NPD5330	Approved
0.7303	Intermediate Similarity	NPD1694	Approved
0.7292	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD7902	Approved
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6672	Approved
0.7065	Intermediate Similarity	NPD5737	Approved
0.7053	Intermediate Similarity	NPD6001	Approved
0.7053	Intermediate Similarity	NPD7748	Approved
0.7037	Intermediate Similarity	NPD229	Approved
0.7033	Intermediate Similarity	NPD3618	Phase 1
0.7021	Intermediate Similarity	NPD6411	Approved
0.6988	Remote Similarity	NPD5777	Approved
0.6966	Remote Similarity	NPD3667	Approved
0.6957	Remote Similarity	NPD3573	Approved
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.6848	Remote Similarity	NPD6098	Approved
0.6842	Remote Similarity	NPD7515	Phase 2
0.6827	Remote Similarity	NPD6373	Approved
0.6827	Remote Similarity	NPD6372	Approved
0.6813	Remote Similarity	NPD4786	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.6809	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6101	Approved
0.6796	Remote Similarity	NPD5697	Approved
0.6796	Remote Similarity	NPD5701	Approved
0.6782	Remote Similarity	NPD6116	Phase 1
0.6768	Remote Similarity	NPD5696	Approved
0.6737	Remote Similarity	NPD5207	Approved
0.6731	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6881	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6731	Remote Similarity	NPD6899	Approved
0.6702	Remote Similarity	NPD5208	Approved
0.6698	Remote Similarity	NPD6649	Approved
0.6698	Remote Similarity	NPD6650	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5695	Phase 3
0.6633	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6673	Approved
0.6632	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD6080	Approved
0.6632	Remote Similarity	NPD6904	Approved
0.663	Remote Similarity	NPD3133	Approved
0.663	Remote Similarity	NPD3665	Phase 1
0.663	Remote Similarity	NPD3666	Approved
0.6628	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7290	Approved
0.6604	Remote Similarity	NPD6883	Approved
0.6604	Remote Similarity	NPD7102	Approved
0.66	Remote Similarity	NPD7638	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6566	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3702	Approved
0.6542	Remote Similarity	NPD8130	Phase 1
0.6542	Remote Similarity	NPD6847	Approved
0.6542	Remote Similarity	NPD6869	Approved
0.6542	Remote Similarity	NPD6617	Approved
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6531	Remote Similarity	NPD5282	Discontinued
0.6522	Remote Similarity	NPD4788	Approved
0.6517	Remote Similarity	NPD6114	Approved
0.6517	Remote Similarity	NPD6697	Approved
0.6517	Remote Similarity	NPD6115	Approved
0.6517	Remote Similarity	NPD6118	Approved
0.65	Remote Similarity	NPD4755	Approved
0.6495	Remote Similarity	NPD6079	Approved
0.6495	Remote Similarity	NPD7637	Suspended
0.6495	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4697	Phase 3
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5692	Phase 3
0.6389	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4224	Phase 2
0.6373	Remote Similarity	NPD5285	Approved
0.6373	Remote Similarity	NPD5286	Approved
0.6373	Remote Similarity	NPD4700	Approved
0.6373	Remote Similarity	NPD4696	Approved
0.6372	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD5694	Approved
0.6327	Remote Similarity	NPD5284	Approved
0.6327	Remote Similarity	NPD5281	Approved
0.6306	Remote Similarity	NPD6274	Approved
0.6304	Remote Similarity	NPD5369	Approved
0.6293	Remote Similarity	NPD7492	Approved
0.6289	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD6051	Approved
0.6289	Remote Similarity	NPD1695	Approved
0.6273	Remote Similarity	NPD8133	Approved
0.6265	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7645	Phase 2
0.6262	Remote Similarity	NPD6686	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD6616	Approved
0.6238	Remote Similarity	NPD5222	Approved
0.6238	Remote Similarity	NPD5221	Approved
0.6238	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4221	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6228	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD6059	Approved
0.6207	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8328	Phase 3
0.6196	Remote Similarity	NPD4695	Discontinued
0.6196	Remote Similarity	NPD7525	Registered
0.619	Remote Similarity	NPD5174	Approved
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD6052	Approved
0.6186	Remote Similarity	NPD8293	Discontinued
0.6186	Remote Similarity	NPD7078	Approved
0.618	Remote Similarity	NPD8039	Approved
0.618	Remote Similarity	NPD3703	Phase 2
0.6176	Remote Similarity	NPD5173	Approved
0.6174	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6015	Approved
0.6174	Remote Similarity	NPD6016	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6163	Remote Similarity	NPD4137	Phase 3
0.6163	Remote Similarity	NPD3698	Phase 2
0.6154	Remote Similarity	NPD3617	Approved
0.6154	Remote Similarity	NPD5223	Approved
0.6147	Remote Similarity	NPD4634	Approved
0.6146	Remote Similarity	NPD5279	Phase 3
0.614	Remote Similarity	NPD7101	Approved
0.614	Remote Similarity	NPD7100	Approved
0.6139	Remote Similarity	NPD4629	Approved
0.6139	Remote Similarity	NPD5210	Approved
0.6134	Remote Similarity	NPD7736	Approved
0.6132	Remote Similarity	NPD5141	Approved
0.6126	Remote Similarity	NPD4632	Approved
0.6122	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6370	Approved
0.6121	Remote Similarity	NPD5988	Approved
0.6111	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6317	Approved
0.6105	Remote Similarity	NPD4197	Approved
0.6095	Remote Similarity	NPD7632	Discontinued
0.6092	Remote Similarity	NPD4244	Approved
0.6092	Remote Similarity	NPD4691	Approved
0.6092	Remote Similarity	NPD4747	Approved
0.6092	Remote Similarity	NPD4245	Approved
0.6075	Remote Similarity	NPD4767	Approved
0.6075	Remote Similarity	NPD4768	Approved
0.6064	Remote Similarity	NPD6435	Approved
0.6064	Remote Similarity	NPD4270	Approved
0.6064	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD5785	Approved
0.6053	Remote Similarity	NPD6335	Approved
0.6053	Remote Similarity	NPD6314	Approved
0.6053	Remote Similarity	NPD6313	Approved
0.6047	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5329	Approved
0.6042	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4754	Approved
0.6034	Remote Similarity	NPD6921	Approved
0.6034	Remote Similarity	NPD6909	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