NPASS Compound

Structure

NPC474854 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 2.8774 -0.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6822 -3.1632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 0.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6167 -0.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1110 0.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5170 -0.6990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -1.2827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9758 -1.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 -2.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9288 -0.5587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 -2.1640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5276 0.2503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7469 -1.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1551 -1.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1616 -2.0016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3508 -0.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -2.0096 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4629 -1.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5464 -2.2787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4196 -2.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4115 -0.7314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 12 2 1 6 0 0 0 12 16 1 0 0 0 0 13 6 1 6 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 1 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.263
LogD:	0.936
LogS:	-2.273
# Rotatable Bonds:	0
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.639
Synthetic Accessibility Score:	5.825
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.72
MDCK Permeability:	1.9922837964259088e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.466
Plasma Protein Binding (PPB):	69.17731475830078%
Volume Distribution (VD):	0.88
Pgp-substrate:	20.620912551879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.487
CYP2C19-inhibitor:	0.373
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.278
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.832
CYP3A4-inhibitor:	0.096
CYP3A4-substrate:	0.398

ADMET: Excretion

Clearance (CL):	12.678
Half-life (T1/2):	0.223

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.575
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.586
Carcinogencity:	0.169
Eye Corrosion:	0.993
Eye Irritation:	0.308
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC474854

Natural Product ID:	NPC474854
*Common Name:**	Cespitularin H
IUPAC Name:	n.a.
Synonyms:	Cespitularin H
Standard InCHIKey:	AXOPQHQNFSMCKW-MNTHUZLMSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11-5-6-13-7-8-15-17(20(13,3)4)19(23)16(18(15)22)12(2)10-14(21)9-11/h5,12-13,16,18,22H,6-10H2,1-4H3/b11-5+/t12-,13+,16-,18-/m0/s1
SMILES:	CC1CC(=O)CC(=CCC2CCC3=C(C2(C)C)C(=O)C1C3O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485069
PubChem CID:	44575971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols 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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	9.32	ug ml-1	PMID[459771]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	23.69	ug ml-1	PMID[459771]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[459771]

☑ 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 NPC474854 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	182
0.1-0.2	1257
0.2-0.3	5733
0.3-0.4	13257
0.4-0.5	11314
0.5-0.6	6776
0.6-0.7	3517
0.7-0.8	625
0.8-0.85	27
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9398	High Similarity	NPC474853
0.9398	High Similarity	NPC179006
0.8837	High Similarity	NPC194417
0.8605	High Similarity	NPC230527
0.8605	High Similarity	NPC7927
0.8571	High Similarity	NPC53685
0.8409	Intermediate Similarity	NPC476043
0.8353	Intermediate Similarity	NPC45495
0.8333	Intermediate Similarity	NPC123912
0.8333	Intermediate Similarity	NPC472971
0.8333	Intermediate Similarity	NPC475994
0.8333	Intermediate Similarity	NPC472970
0.828	Intermediate Similarity	NPC472932
0.8261	Intermediate Similarity	NPC69454
0.8261	Intermediate Similarity	NPC472930
0.8235	Intermediate Similarity	NPC308038
0.8235	Intermediate Similarity	NPC7232
0.8211	Intermediate Similarity	NPC147954
0.8193	Intermediate Similarity	NPC474011
0.8152	Intermediate Similarity	NPC63748
0.814	Intermediate Similarity	NPC104120
0.814	Intermediate Similarity	NPC157895
0.814	Intermediate Similarity	NPC148685
0.8132	Intermediate Similarity	NPC309603
0.8132	Intermediate Similarity	NPC473999
0.8125	Intermediate Similarity	NPC51370
0.8125	Intermediate Similarity	NPC287833
0.8118	Intermediate Similarity	NPC62336
0.8095	Intermediate Similarity	NPC469646
0.8095	Intermediate Similarity	NPC263582
0.809	Intermediate Similarity	NPC36350
0.809	Intermediate Similarity	NPC471224
0.809	Intermediate Similarity	NPC474083
0.809	Intermediate Similarity	NPC476426
0.8085	Intermediate Similarity	NPC259286
0.8068	Intermediate Similarity	NPC105173
0.8065	Intermediate Similarity	NPC477520
0.8043	Intermediate Similarity	NPC230332
0.8043	Intermediate Similarity	NPC48010
0.8041	Intermediate Similarity	NPC472924
0.8022	Intermediate Similarity	NPC328539
0.8022	Intermediate Similarity	NPC476796
0.8021	Intermediate Similarity	NPC197386
0.8021	Intermediate Similarity	NPC471717
0.8	Intermediate Similarity	NPC184065
0.8	Intermediate Similarity	NPC74995
0.8	Intermediate Similarity	NPC472941
0.8	Intermediate Similarity	NPC456
0.8	Intermediate Similarity	NPC470955
0.8	Intermediate Similarity	NPC469994
0.8	Intermediate Similarity	NPC249954
0.7978	Intermediate Similarity	NPC85774
0.7978	Intermediate Similarity	NPC161423
0.7978	Intermediate Similarity	NPC329043
0.7978	Intermediate Similarity	NPC227064
0.7978	Intermediate Similarity	NPC476412
0.7978	Intermediate Similarity	NPC58841
0.7978	Intermediate Similarity	NPC473246
0.7978	Intermediate Similarity	NPC321187
0.7978	Intermediate Similarity	NPC214043
0.7976	Intermediate Similarity	NPC114236
0.7957	Intermediate Similarity	NPC475806
0.7957	Intermediate Similarity	NPC473998
0.7955	Intermediate Similarity	NPC93590
0.7952	Intermediate Similarity	NPC186042
0.7935	Intermediate Similarity	NPC170775
0.7935	Intermediate Similarity	NPC477943
0.7935	Intermediate Similarity	NPC275740
0.7935	Intermediate Similarity	NPC86319
0.7935	Intermediate Similarity	NPC214387
0.7935	Intermediate Similarity	NPC472973
0.7935	Intermediate Similarity	NPC2983
0.7931	Intermediate Similarity	NPC824
0.7931	Intermediate Similarity	NPC233352
0.7931	Intermediate Similarity	NPC172013
0.7931	Intermediate Similarity	NPC306095
0.7931	Intermediate Similarity	NPC138492
0.7912	Intermediate Similarity	NPC312561
0.7907	Intermediate Similarity	NPC297996
0.7895	Intermediate Similarity	NPC174948
0.7895	Intermediate Similarity	NPC318282
0.7895	Intermediate Similarity	NPC173875
0.7895	Intermediate Similarity	NPC469995
0.7895	Intermediate Similarity	NPC37646
0.7889	Intermediate Similarity	NPC469948
0.7872	Intermediate Similarity	NPC474736
0.7872	Intermediate Similarity	NPC115021
0.7865	Intermediate Similarity	NPC41539
0.7865	Intermediate Similarity	NPC62214
0.7865	Intermediate Similarity	NPC474748
0.7865	Intermediate Similarity	NPC476082
0.7865	Intermediate Similarity	NPC278648
0.7865	Intermediate Similarity	NPC64600
0.7857	Intermediate Similarity	NPC215050
0.7849	Intermediate Similarity	NPC69622
0.7849	Intermediate Similarity	NPC134321
0.7849	Intermediate Similarity	NPC477149
0.7849	Intermediate Similarity	NPC477147
0.7841	Intermediate Similarity	NPC136150
0.7841	Intermediate Similarity	NPC116797
0.7841	Intermediate Similarity	NPC189237
0.7826	Intermediate Similarity	NPC143767
0.7826	Intermediate Similarity	NPC328313
0.7826	Intermediate Similarity	NPC53911
0.7826	Intermediate Similarity	NPC131470
0.7822	Intermediate Similarity	NPC185
0.7816	Intermediate Similarity	NPC281138
0.7816	Intermediate Similarity	NPC152061
0.7812	Intermediate Similarity	NPC3772
0.7812	Intermediate Similarity	NPC117133
0.7812	Intermediate Similarity	NPC243525
0.7812	Intermediate Similarity	NPC40765
0.7812	Intermediate Similarity	NPC328371
0.7812	Intermediate Similarity	NPC473164
0.7802	Intermediate Similarity	NPC145879
0.7802	Intermediate Similarity	NPC327115
0.7802	Intermediate Similarity	NPC472986
0.7802	Intermediate Similarity	NPC472974
0.7802	Intermediate Similarity	NPC474778
0.7802	Intermediate Similarity	NPC472985
0.7802	Intermediate Similarity	NPC474732
0.7802	Intermediate Similarity	NPC474733
0.7802	Intermediate Similarity	NPC31564
0.7791	Intermediate Similarity	NPC86917
0.7791	Intermediate Similarity	NPC197659
0.7791	Intermediate Similarity	NPC276769
0.7789	Intermediate Similarity	NPC8993
0.7789	Intermediate Similarity	NPC473162
0.7778	Intermediate Similarity	NPC195290
0.7778	Intermediate Similarity	NPC473424
0.7778	Intermediate Similarity	NPC82902
0.7778	Intermediate Similarity	NPC204450
0.7778	Intermediate Similarity	NPC477915
0.7778	Intermediate Similarity	NPC165064
0.7778	Intermediate Similarity	NPC237712
0.7778	Intermediate Similarity	NPC227132
0.7778	Intermediate Similarity	NPC87351
0.7766	Intermediate Similarity	NPC168027
0.7766	Intermediate Similarity	NPC233116
0.7766	Intermediate Similarity	NPC185936
0.7766	Intermediate Similarity	NPC472978
0.7766	Intermediate Similarity	NPC172101
0.7755	Intermediate Similarity	NPC306856
0.7755	Intermediate Similarity	NPC476274
0.7755	Intermediate Similarity	NPC110149
0.7753	Intermediate Similarity	NPC477271
0.7753	Intermediate Similarity	NPC129080
0.7753	Intermediate Similarity	NPC46881
0.7753	Intermediate Similarity	NPC20262
0.7753	Intermediate Similarity	NPC477270
0.7753	Intermediate Similarity	NPC256750
0.7753	Intermediate Similarity	NPC477269
0.7742	Intermediate Similarity	NPC186688
0.7742	Intermediate Similarity	NPC472475
0.7742	Intermediate Similarity	NPC472983
0.7742	Intermediate Similarity	NPC472477
0.7742	Intermediate Similarity	NPC119416
0.7732	Intermediate Similarity	NPC473161
0.7732	Intermediate Similarity	NPC53844
0.7732	Intermediate Similarity	NPC106557
0.7732	Intermediate Similarity	NPC69385
0.7732	Intermediate Similarity	NPC121339
0.7727	Intermediate Similarity	NPC74445
0.7727	Intermediate Similarity	NPC472478
0.7727	Intermediate Similarity	NPC271104
0.7727	Intermediate Similarity	NPC2482
0.7727	Intermediate Similarity	NPC287817
0.7717	Intermediate Similarity	NPC317590
0.7717	Intermediate Similarity	NPC272039
0.7717	Intermediate Similarity	NPC136548
0.7717	Intermediate Similarity	NPC287079
0.7717	Intermediate Similarity	NPC475740
0.7717	Intermediate Similarity	NPC58063
0.7717	Intermediate Similarity	NPC220930
0.7708	Intermediate Similarity	NPC271195
0.7701	Intermediate Similarity	NPC471409
0.7701	Intermediate Similarity	NPC178852
0.7701	Intermediate Similarity	NPC478122
0.7701	Intermediate Similarity	NPC275494
0.77	Intermediate Similarity	NPC111323
0.77	Intermediate Similarity	NPC236390
0.77	Intermediate Similarity	NPC311612
0.7692	Intermediate Similarity	NPC274724
0.7692	Intermediate Similarity	NPC472931
0.7692	Intermediate Similarity	NPC474218
0.7692	Intermediate Similarity	NPC15807
0.7692	Intermediate Similarity	NPC472928
0.7692	Intermediate Similarity	NPC472940
0.7692	Intermediate Similarity	NPC202868
0.7684	Intermediate Similarity	NPC109414
0.7684	Intermediate Similarity	NPC233118
0.7684	Intermediate Similarity	NPC109305
0.7684	Intermediate Similarity	NPC474807
0.7684	Intermediate Similarity	NPC472942
0.7677	Intermediate Similarity	NPC224720
0.7677	Intermediate Similarity	NPC476223
0.7677	Intermediate Similarity	NPC476240
0.7674	Intermediate Similarity	NPC470525
0.767	Intermediate Similarity	NPC470615
0.7667	Intermediate Similarity	NPC472498

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 NPC474854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1922
0.2-0.3	3958
0.3-0.4	2156
0.4-0.5	551
0.5-0.6	261
0.6-0.7	113
0.7-0.8	20
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
0.7978	Intermediate Similarity	NPD3666	Approved
0.7978	Intermediate Similarity	NPD3133	Approved
0.7978	Intermediate Similarity	NPD3665	Phase 1
0.7935	Intermediate Similarity	NPD5328	Approved
0.7766	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD3618	Phase 1
0.7609	Intermediate Similarity	NPD4519	Discontinued
0.7609	Intermediate Similarity	NPD4623	Approved
0.7609	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD5211	Phase 2
0.7582	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD4223	Phase 3
0.7556	Intermediate Similarity	NPD3667	Approved
0.7556	Intermediate Similarity	NPD4221	Approved
0.7553	Intermediate Similarity	NPD4753	Phase 2
0.7551	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD5210	Approved
0.7526	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7451	Intermediate Similarity	NPD5141	Approved
0.7449	Intermediate Similarity	NPD5221	Approved
0.7449	Intermediate Similarity	NPD4697	Phase 3
0.7449	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5222	Approved
0.74	Intermediate Similarity	NPD4700	Approved
0.74	Intermediate Similarity	NPD5286	Approved
0.74	Intermediate Similarity	NPD4696	Approved
0.74	Intermediate Similarity	NPD5285	Approved
0.7391	Intermediate Similarity	NPD4197	Approved
0.7374	Intermediate Similarity	NPD5173	Approved
0.7327	Intermediate Similarity	NPD5223	Approved
0.7312	Intermediate Similarity	NPD1696	Phase 3
0.7312	Intermediate Similarity	NPD5329	Approved
0.7255	Intermediate Similarity	NPD5225	Approved
0.7255	Intermediate Similarity	NPD4633	Approved
0.7255	Intermediate Similarity	NPD5226	Approved
0.7255	Intermediate Similarity	NPD5224	Approved
0.7234	Intermediate Similarity	NPD4689	Approved
0.7234	Intermediate Similarity	NPD5205	Approved
0.7234	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4693	Phase 3
0.7234	Intermediate Similarity	NPD4694	Approved
0.7234	Intermediate Similarity	NPD5280	Approved
0.7234	Intermediate Similarity	NPD4690	Approved
0.7234	Intermediate Similarity	NPD5690	Phase 2
0.7234	Intermediate Similarity	NPD4688	Approved
0.7234	Intermediate Similarity	NPD4138	Approved
0.7184	Intermediate Similarity	NPD4754	Approved
0.7184	Intermediate Similarity	NPD5174	Approved
0.7184	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5696	Approved
0.7128	Intermediate Similarity	NPD5363	Approved
0.7113	Intermediate Similarity	NPD5785	Approved
0.7111	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4634	Approved
0.7053	Intermediate Similarity	NPD5786	Approved
0.7053	Intermediate Similarity	NPD7521	Approved
0.7053	Intermediate Similarity	NPD7334	Approved
0.7053	Intermediate Similarity	NPD6684	Approved
0.7053	Intermediate Similarity	NPD5330	Approved
0.7053	Intermediate Similarity	NPD6409	Approved
0.7053	Intermediate Similarity	NPD7146	Approved
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD4768	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7048	Intermediate Similarity	NPD4767	Approved
0.7041	Intermediate Similarity	NPD7515	Phase 2
0.703	Intermediate Similarity	NPD6084	Phase 2
0.703	Intermediate Similarity	NPD6083	Phase 2
0.7024	Intermediate Similarity	NPD7331	Phase 2
0.7	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5695	Phase 3
0.6989	Remote Similarity	NPD4270	Approved
0.6989	Remote Similarity	NPD4269	Approved
0.6981	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.697	Remote Similarity	NPD5779	Approved
0.697	Remote Similarity	NPD5778	Approved
0.6957	Remote Similarity	NPD4695	Discontinued
0.6923	Remote Similarity	NPD3617	Approved
0.6916	Remote Similarity	NPD4730	Approved
0.6916	Remote Similarity	NPD6011	Approved
0.6916	Remote Similarity	NPD5128	Approved
0.6916	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD6881	Approved
0.6916	Remote Similarity	NPD6899	Approved
0.6916	Remote Similarity	NPD4729	Approved
0.6915	Remote Similarity	NPD4788	Approved
0.6915	Remote Similarity	NPD5362	Discontinued
0.6907	Remote Similarity	NPD6903	Approved
0.6907	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7341	Phase 2
0.6869	Remote Similarity	NPD6411	Approved
0.6869	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD5284	Approved
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6848	Remote Similarity	NPD4195	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6809	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6399	Phase 3
0.6789	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7102	Approved
0.6789	Remote Similarity	NPD7290	Approved
0.6789	Remote Similarity	NPD5251	Approved
0.6789	Remote Similarity	NPD5169	Approved
0.6789	Remote Similarity	NPD6883	Approved
0.6789	Remote Similarity	NPD5248	Approved
0.6789	Remote Similarity	NPD5250	Approved
0.6789	Remote Similarity	NPD5135	Approved
0.6789	Remote Similarity	NPD5249	Phase 3
0.6789	Remote Similarity	NPD5247	Approved
0.6774	Remote Similarity	NPD4252	Approved
0.6768	Remote Similarity	NPD4096	Approved
0.6759	Remote Similarity	NPD5168	Approved
0.6735	Remote Similarity	NPD5737	Approved
0.6735	Remote Similarity	NPD4518	Approved
0.6735	Remote Similarity	NPD6672	Approved
0.6733	Remote Similarity	NPD7748	Approved
0.6733	Remote Similarity	NPD5282	Discontinued
0.6727	Remote Similarity	NPD8130	Phase 1
0.6727	Remote Similarity	NPD6869	Approved
0.6727	Remote Similarity	NPD6649	Approved
0.6727	Remote Similarity	NPD6847	Approved
0.6727	Remote Similarity	NPD6617	Approved
0.6727	Remote Similarity	NPD5127	Approved
0.6727	Remote Similarity	NPD5215	Approved
0.6727	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5217	Approved
0.6727	Remote Similarity	NPD5216	Approved
0.6727	Remote Similarity	NPD6650	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD4747	Approved
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6635	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5133	Approved
0.6633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD5091	Approved
0.6598	Remote Similarity	NPD1694	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6591	Remote Similarity	NPD4137	Phase 3
0.6571	Remote Similarity	NPD7640	Approved
0.6571	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD5208	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD6319	Approved
0.6549	Remote Similarity	NPD5167	Approved
0.6538	Remote Similarity	NPD7902	Approved
0.6535	Remote Similarity	NPD5693	Phase 1
0.6526	Remote Similarity	NPD5369	Approved
0.6518	Remote Similarity	NPD6053	Discontinued
0.6517	Remote Similarity	NPD4691	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6904	Approved
0.6496	Remote Similarity	NPD6015	Approved
0.6496	Remote Similarity	NPD6016	Approved
0.6491	Remote Similarity	NPD6274	Approved
0.6484	Remote Similarity	NPD5733	Approved
0.6484	Remote Similarity	NPD4687	Approved
0.6476	Remote Similarity	NPD7638	Approved
0.6465	Remote Similarity	NPD3573	Approved
0.6458	Remote Similarity	NPD5209	Approved
0.6458	Remote Similarity	NPD6435	Approved
0.6444	Remote Similarity	NPD5276	Approved
0.6442	Remote Similarity	NPD7614	Phase 1
0.6441	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6436	Remote Similarity	NPD5692	Phase 3
0.6436	Remote Similarity	NPD5207	Approved
0.6435	Remote Similarity	NPD6009	Approved
0.6435	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6404	Discontinued
0.6413	Remote Similarity	NPD8264	Approved
0.6392	Remote Similarity	NPD7154	Phase 3
0.6392	Remote Similarity	NPD5331	Approved
0.6392	Remote Similarity	NPD5332	Approved
0.6383	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6335	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