NPASS Compound

Structure

NPC474490 OpenBabel07101719512D 27 28 0 0 1 0 0 0 0 0999 V2000 5.5171 1.3372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7901 -1.9527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1367 -3.0578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8454 -2.7740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8735 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 0.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 0.4556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5862 1.7026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8013 -1.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9459 -1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9865 0.1638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6802 0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9092 -2.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8044 1.0791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 -1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4471 -0.7238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6774 0.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7453 -1.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1490 -0.9888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9534 0.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2407 -0.1679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9403 -2.4860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1774 1.5243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8843 -0.2751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4360 -0.8728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1716 -0.5333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 8 14 2 0 0 0 0 9 26 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 16 18 1 0 0 0 0 16 26 1 1 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 19 2 0 0 0 0 19 21 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 6 1 1 0 0 0 22 7 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	2.9
LogD:	2.459
LogS:	-4.329
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	4.683
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.66
MDCK Permeability:	2.3907297872938216e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.882
30% Bioavailability (F30%):	0.876

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.418
Plasma Protein Binding (PPB):	91.14592742919922%
Volume Distribution (VD):	0.845
Pgp-substrate:	9.8719482421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.474
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.449
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	8.747
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.239
Drug-inuced Liver Injury (DILI):	0.534
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.129
Skin Sensitization:	0.192
Carcinogencity:	0.67
Eye Corrosion:	0.029
Eye Irritation:	0.138
Respiratory Toxicity:	0.586

Download Data

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

Natural Product: NPC474490

Natural Product ID:	NPC474490
*Common Name:**	(1R,3S,8S)-3-Ethoxy-8-Angeloyloxydauca-4-En-9-One
IUPAC Name:	[(2S,6S,8aR)-2-ethoxy-6,8a-dimethyl-4,7-dioxo-3-propan-2-yl-1,2,5,8-tetrahydroazulen-6-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	FHWTXEUDQYBBHR-NUAIMQSUSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-8-14(5)20(25)27-22(7)10-15(23)19-18(13(3)4)16(26-9-2)11-21(19,6)12-17(22)24/h8,13,16H,9-12H2,1-7H3/b14-8-/t16-,21+,22-/m0/s1
SMILES:	CCO[C@H]1C[C@]2(C(=C1C(C)C)C(=O)C[C@](C(=O)C2)(C)OC(=O)/C(=CC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469918
PubChem CID:	44575421
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277769]
NPO33190	ferula hermonis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787464]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	223.9	%	PMID[544161]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	321.4	%	PMID[544161]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	974.4	%	PMID[544161]

☑ 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 NPC474490 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	257
0.1-0.2	1892
0.2-0.3	7096
0.3-0.4	13650
0.4-0.5	10964
0.5-0.6	6125
0.6-0.7	2409
0.7-0.8	285
0.8-0.85	15
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC38576
0.8667	High Similarity	NPC279859
0.8646	High Similarity	NPC54843
0.8478	Intermediate Similarity	NPC471047
0.8478	Intermediate Similarity	NPC469628
0.8478	Intermediate Similarity	NPC469631
0.8478	Intermediate Similarity	NPC475906
0.8478	Intermediate Similarity	NPC469653
0.8421	Intermediate Similarity	NPC148463
0.8211	Intermediate Similarity	NPC284185
0.8105	Intermediate Similarity	NPC253144
0.8105	Intermediate Similarity	NPC471818
0.8085	Intermediate Similarity	NPC475902
0.8041	Intermediate Similarity	NPC469632
0.8022	Intermediate Similarity	NPC471326
0.8022	Intermediate Similarity	NPC221231
0.8021	Intermediate Similarity	NPC74103
0.8021	Intermediate Similarity	NPC70595
0.8021	Intermediate Similarity	NPC150978
0.8021	Intermediate Similarity	NPC123177
0.7979	Intermediate Similarity	NPC478144
0.7979	Intermediate Similarity	NPC478145
0.7935	Intermediate Similarity	NPC215294
0.7917	Intermediate Similarity	NPC77337
0.7889	Intermediate Similarity	NPC469620
0.7889	Intermediate Similarity	NPC469690
0.7879	Intermediate Similarity	NPC476275
0.7872	Intermediate Similarity	NPC261721
0.7835	Intermediate Similarity	NPC20713
0.7835	Intermediate Similarity	NPC221282
0.7778	Intermediate Similarity	NPC470978
0.7778	Intermediate Similarity	NPC470974
0.7767	Intermediate Similarity	NPC472755
0.7767	Intermediate Similarity	NPC475873
0.7766	Intermediate Similarity	NPC21471
0.7766	Intermediate Similarity	NPC161957
0.7766	Intermediate Similarity	NPC33570
0.7745	Intermediate Similarity	NPC472753
0.7745	Intermediate Similarity	NPC477950
0.7732	Intermediate Similarity	NPC469718
0.7732	Intermediate Similarity	NPC329857
0.7723	Intermediate Similarity	NPC470188
0.7723	Intermediate Similarity	NPC141191
0.7717	Intermediate Similarity	NPC286229
0.77	Intermediate Similarity	NPC184065
0.77	Intermediate Similarity	NPC121036
0.77	Intermediate Similarity	NPC472674
0.77	Intermediate Similarity	NPC185553
0.7692	Intermediate Similarity	NPC471740
0.7692	Intermediate Similarity	NPC472756
0.7684	Intermediate Similarity	NPC104961
0.7684	Intermediate Similarity	NPC70555
0.7684	Intermediate Similarity	NPC474045
0.7684	Intermediate Similarity	NPC469676
0.7684	Intermediate Similarity	NPC261253
0.7684	Intermediate Similarity	NPC70422
0.7677	Intermediate Similarity	NPC167219
0.767	Intermediate Similarity	NPC472754
0.766	Intermediate Similarity	NPC238197
0.766	Intermediate Similarity	NPC149869
0.7653	Intermediate Similarity	NPC219874
0.7653	Intermediate Similarity	NPC290651
0.7634	Intermediate Similarity	NPC173609
0.7624	Intermediate Similarity	NPC169205
0.7624	Intermediate Similarity	NPC170143
0.7624	Intermediate Similarity	NPC213947
0.7624	Intermediate Similarity	NPC108475
0.7624	Intermediate Similarity	NPC477949
0.7609	Intermediate Similarity	NPC223904
0.7604	Intermediate Similarity	NPC471739
0.76	Intermediate Similarity	NPC474947
0.76	Intermediate Similarity	NPC90121
0.76	Intermediate Similarity	NPC275960
0.76	Intermediate Similarity	NPC48803
0.76	Intermediate Similarity	NPC193645
0.7593	Intermediate Similarity	NPC475495
0.7582	Intermediate Similarity	NPC128276
0.7579	Intermediate Similarity	NPC96621
0.7576	Intermediate Similarity	NPC202824
0.7576	Intermediate Similarity	NPC475302
0.7576	Intermediate Similarity	NPC477361
0.7576	Intermediate Similarity	NPC165383
0.7573	Intermediate Similarity	NPC133907
0.7573	Intermediate Similarity	NPC110443
0.7573	Intermediate Similarity	NPC128733
0.7573	Intermediate Similarity	NPC474742
0.7573	Intermediate Similarity	NPC46998
0.7573	Intermediate Similarity	NPC185141
0.7553	Intermediate Similarity	NPC39588
0.7551	Intermediate Similarity	NPC145666
0.7527	Intermediate Similarity	NPC275507
0.7527	Intermediate Similarity	NPC10276
0.7527	Intermediate Similarity	NPC471325
0.7527	Intermediate Similarity	NPC35089
0.7525	Intermediate Similarity	NPC477354
0.7523	Intermediate Similarity	NPC477093
0.7523	Intermediate Similarity	NPC473522
0.7523	Intermediate Similarity	NPC475277
0.75	Intermediate Similarity	NPC107787
0.75	Intermediate Similarity	NPC622
0.75	Intermediate Similarity	NPC49393
0.75	Intermediate Similarity	NPC25639
0.75	Intermediate Similarity	NPC476596
0.75	Intermediate Similarity	NPC118405
0.75	Intermediate Similarity	NPC65829
0.75	Intermediate Similarity	NPC276647
0.75	Intermediate Similarity	NPC105725
0.75	Intermediate Similarity	NPC238593
0.75	Intermediate Similarity	NPC121825
0.7475	Intermediate Similarity	NPC111114
0.7475	Intermediate Similarity	NPC300312
0.7475	Intermediate Similarity	NPC261607
0.7474	Intermediate Similarity	NPC115786
0.7474	Intermediate Similarity	NPC474359
0.7474	Intermediate Similarity	NPC475796
0.7473	Intermediate Similarity	NPC57744
0.7473	Intermediate Similarity	NPC122264
0.7473	Intermediate Similarity	NPC180290
0.7451	Intermediate Similarity	NPC47834
0.7449	Intermediate Similarity	NPC280833
0.7447	Intermediate Similarity	NPC85772
0.7444	Intermediate Similarity	NPC216791
0.7444	Intermediate Similarity	NPC244166
0.7429	Intermediate Similarity	NPC475945
0.7429	Intermediate Similarity	NPC475871
0.7429	Intermediate Similarity	NPC110989
0.7423	Intermediate Similarity	NPC471738
0.7419	Intermediate Similarity	NPC302426
0.7419	Intermediate Similarity	NPC74673
0.7419	Intermediate Similarity	NPC69271
0.7404	Intermediate Similarity	NPC195192
0.7404	Intermediate Similarity	NPC206079
0.7404	Intermediate Similarity	NPC475099
0.7404	Intermediate Similarity	NPC171759
0.7404	Intermediate Similarity	NPC304738
0.74	Intermediate Similarity	NPC476598
0.74	Intermediate Similarity	NPC135776
0.74	Intermediate Similarity	NPC476597
0.74	Intermediate Similarity	NPC469645
0.74	Intermediate Similarity	NPC469692
0.7396	Intermediate Similarity	NPC472686
0.7396	Intermediate Similarity	NPC261380
0.7396	Intermediate Similarity	NPC290329
0.7396	Intermediate Similarity	NPC78089
0.7396	Intermediate Similarity	NPC476628
0.7396	Intermediate Similarity	NPC197903
0.7396	Intermediate Similarity	NPC99395
0.7391	Intermediate Similarity	NPC192309
0.7391	Intermediate Similarity	NPC471220
0.7391	Intermediate Similarity	NPC253749
0.7391	Intermediate Similarity	NPC299235
0.7383	Intermediate Similarity	NPC470192
0.7383	Intermediate Similarity	NPC26617
0.7379	Intermediate Similarity	NPC222011
0.7374	Intermediate Similarity	NPC306168
0.7374	Intermediate Similarity	NPC49946
0.7374	Intermediate Similarity	NPC62815
0.7368	Intermediate Similarity	NPC475947
0.7368	Intermediate Similarity	NPC222358
0.7368	Intermediate Similarity	NPC170377
0.7368	Intermediate Similarity	NPC474703
0.7368	Intermediate Similarity	NPC54468
0.7368	Intermediate Similarity	NPC318468
0.7358	Intermediate Similarity	NPC474741
0.7358	Intermediate Similarity	NPC203659
0.7358	Intermediate Similarity	NPC100487
0.7358	Intermediate Similarity	NPC309190
0.7353	Intermediate Similarity	NPC9812
0.734	Intermediate Similarity	NPC301477
0.734	Intermediate Similarity	NPC42470
0.734	Intermediate Similarity	NPC281949
0.734	Intermediate Similarity	NPC25684
0.7339	Intermediate Similarity	NPC477103
0.7333	Intermediate Similarity	NPC225353
0.7333	Intermediate Similarity	NPC474747
0.7328	Intermediate Similarity	NPC1538
0.7327	Intermediate Similarity	NPC53685
0.7327	Intermediate Similarity	NPC84893
0.732	Intermediate Similarity	NPC220478
0.7312	Intermediate Similarity	NPC178277
0.7312	Intermediate Similarity	NPC472013
0.7312	Intermediate Similarity	NPC476624
0.7308	Intermediate Similarity	NPC469551
0.7308	Intermediate Similarity	NPC280963
0.7308	Intermediate Similarity	NPC174314
0.73	Intermediate Similarity	NPC45579
0.73	Intermediate Similarity	NPC191339
0.73	Intermediate Similarity	NPC286341
0.73	Intermediate Similarity	NPC472705
0.7297	Intermediate Similarity	NPC472929
0.7292	Intermediate Similarity	NPC475100
0.7283	Intermediate Similarity	NPC470240
0.7283	Intermediate Similarity	NPC65603
0.7283	Intermediate Similarity	NPC476794
0.7282	Intermediate Similarity	NPC87090
0.7282	Intermediate Similarity	NPC69385
0.7273	Intermediate Similarity	NPC117405
0.7273	Intermediate Similarity	NPC78008
0.7273	Intermediate Similarity	NPC268298
0.7273	Intermediate Similarity	NPC52198

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 NPC474490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	2439
0.2-0.3	3888
0.3-0.4	1758
0.4-0.5	534
0.5-0.6	227
0.6-0.7	45
0.7-0.8	3
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
0.76	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5209	Approved
0.7383	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5785	Approved
0.7182	Intermediate Similarity	NPD6371	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7083	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.697	Remote Similarity	NPD5786	Approved
0.6931	Remote Similarity	NPD6673	Approved
0.6931	Remote Similarity	NPD6904	Approved
0.6931	Remote Similarity	NPD6080	Approved
0.6887	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD1694	Approved
0.6869	Remote Similarity	NPD5363	Approved
0.6847	Remote Similarity	NPD6881	Approved
0.6847	Remote Similarity	NPD6899	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6814	Remote Similarity	NPD6649	Approved
0.6814	Remote Similarity	NPD6650	Approved
0.68	Remote Similarity	NPD6409	Approved
0.68	Remote Similarity	NPD7521	Approved
0.68	Remote Similarity	NPD6684	Approved
0.68	Remote Similarity	NPD7334	Approved
0.68	Remote Similarity	NPD7146	Approved
0.68	Remote Similarity	NPD5330	Approved
0.6796	Remote Similarity	NPD6050	Approved
0.6792	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6083	Phase 2
0.6786	Remote Similarity	NPD6373	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6765	Remote Similarity	NPD1695	Approved
0.6762	Remote Similarity	NPD5695	Phase 3
0.6757	Remote Similarity	NPD5697	Approved
0.6726	Remote Similarity	NPD7290	Approved
0.6726	Remote Similarity	NPD6883	Approved
0.6726	Remote Similarity	NPD7102	Approved
0.6699	Remote Similarity	NPD5692	Phase 3
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6635	Remote Similarity	NPD5694	Approved
0.6634	Remote Similarity	NPD6098	Approved
0.6633	Remote Similarity	NPD5369	Approved
0.6609	Remote Similarity	NPD6882	Approved
0.6609	Remote Similarity	NPD8297	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6566	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4270	Approved
0.6566	Remote Similarity	NPD6435	Approved
0.6566	Remote Similarity	NPD4269	Approved
0.6535	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8039	Approved
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD7154	Phase 3
0.65	Remote Similarity	NPD5362	Discontinued
0.6495	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6614	Approved
0.6444	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD4252	Approved
0.6364	Remote Similarity	NPD5368	Approved
0.6364	Remote Similarity	NPD6319	Approved
0.6333	Remote Similarity	NPD6335	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD6411	Approved
0.6303	Remote Similarity	NPD6274	Approved
0.6296	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5654	Approved
0.6296	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD4629	Approved
0.629	Remote Similarity	NPD7492	Approved
0.6286	Remote Similarity	NPD6051	Approved
0.6281	Remote Similarity	NPD7101	Approved
0.6281	Remote Similarity	NPD7100	Approved
0.6273	Remote Similarity	NPD7638	Approved
0.6273	Remote Similarity	NPD4225	Approved
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD6399	Phase 3
0.6262	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD3573	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6317	Approved
0.624	Remote Similarity	NPD6616	Approved
0.623	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD6008	Approved
0.6226	Remote Similarity	NPD6698	Approved
0.6226	Remote Similarity	NPD46	Approved
0.6216	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD7640	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.6214	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7900	Approved
0.6204	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.619	Remote Similarity	NPD5208	Approved
0.619	Remote Similarity	NPD7078	Approved
0.6182	Remote Similarity	NPD5959	Approved
0.6182	Remote Similarity	NPD4755	Approved
0.6168	Remote Similarity	NPD7983	Approved
0.6167	Remote Similarity	NPD6868	Approved
0.6161	Remote Similarity	NPD5223	Approved
0.6142	Remote Similarity	NPD7736	Approved
0.614	Remote Similarity	NPD5141	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6132	Remote Similarity	NPD6101	Approved
0.6132	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD6370	Approved
0.6124	Remote Similarity	NPD7260	Phase 2
0.6121	Remote Similarity	NPD6686	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4633	Approved
0.6106	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD6059	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.608	Remote Similarity	NPD7604	Phase 2
0.6075	Remote Similarity	NPD5207	Approved
0.6071	Remote Similarity	NPD4700	Approved
0.6063	Remote Similarity	NPD8293	Discontinued
0.6061	Remote Similarity	NPD4756	Discovery
0.6058	Remote Similarity	NPD5329	Approved
0.6055	Remote Similarity	NPD7748	Approved
0.6053	Remote Similarity	NPD5175	Approved
0.6053	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD6908	Approved
0.6048	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD6909	Approved
0.6048	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.604	Remote Similarity	NPD4819	Approved
0.604	Remote Similarity	NPD4822	Approved
0.604	Remote Similarity	NPD4821	Approved
0.604	Remote Similarity	NPD4820	Approved
0.604	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7902	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6022	Remote Similarity	NPD7331	Phase 2
0.6019	Remote Similarity	NPD6079	Approved
0.6017	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5690	Phase 2
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5981	Remote Similarity	NPD5328	Approved
0.5969	Remote Similarity	NPD7319	Approved
0.5962	Remote Similarity	NPD4197	Approved
0.5962	Remote Similarity	NPD3133	Approved
0.5962	Remote Similarity	NPD3666	Approved
0.5962	Remote Similarity	NPD3665	Phase 1
0.5946	Remote Similarity	NPD7732	Phase 3
0.5946	Remote Similarity	NPD7839	Suspended
0.5926	Remote Similarity	NPD7838	Discovery
0.592	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7341	Phase 2
0.5913	Remote Similarity	NPD4754	Approved
0.5909	Remote Similarity	NPD6001	Approved
0.5896	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4695	Discontinued
0.5872	Remote Similarity	NPD5284	Approved
0.5872	Remote Similarity	NPD5281	Approved
0.5872	Remote Similarity	NPD7637	Suspended
0.5872	Remote Similarity	NPD7515	Phase 2
0.5865	Remote Similarity	NPD5331	Approved
0.5865	Remote Similarity	NPD5332	Approved
0.5859	Remote Similarity	NPD7507	Approved
0.5851	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5280	Approved
0.5849	Remote Similarity	NPD4694	Approved
0.5847	Remote Similarity	NPD4729	Approved
0.5847	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD4730	Approved
0.5847	Remote Similarity	NPD5128	Approved
0.5842	Remote Similarity	NPD4271	Approved
0.5842	Remote Similarity	NPD4268	Approved
0.5841	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5370	Suspended
0.5833	Remote Similarity	NPD6845	Suspended

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