NPASS Compound

Structure

NPC472008 OpenBabel07101719512D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5731 -3.9392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5731 0.2071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6589 -2.0731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 13 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 15 2 0 0 0 0 11 1 1 1 0 0 0 11 23 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.14
Volume:	325.034
LogP:	1.622
LogD:	1.011
LogS:	-3.692
# Rotatable Bonds:	1
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	4.346
Fsp3:	0.588
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:	-4.733
MDCK Permeability:	2.457272603351157e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.694
30% Bioavailability (F30%):	0.191

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	80.92479705810547%
Volume Distribution (VD):	0.975
Pgp-substrate:	10.54786205291748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.396
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.736

ADMET: Excretion

Clearance (CL):	2.241
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.621
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.828
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.803
Skin Sensitization:	0.276
Carcinogencity:	0.539
Eye Corrosion:	0.035
Eye Irritation:	0.777
Respiratory Toxicity:	0.44

Download Data

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

Natural Product: NPC472008

Natural Product ID:	NPC472008
*Common Name:**	NCGPVJGWUGDOHF-PIGZYNQJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NCGPVJGWUGDOHF-PIGZYNQJSA-N
Standard InCHI:	InChI=1S/C17H22O6/c1-11-5-3-7-13(18)8-4-6-12-9-14(19)10-15(22-2)17(12,21)16(20)23-11/h9-11,21H,3-8H2,1-2H3/t11-,17-/m1/s1
SMILES:	COC1=CC(=O)C=C2[C@]1(O)C(=O)O[C@H](C)CCCC(=O)CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3319024
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32516	ficus auriculata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25008455]

☑ 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
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	10.0	%	PMID[539085]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8.94	%	PMID[539085]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	2.61	%	PMID[539085]

☑ 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 NPC472008 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	199
0.1-0.2	1280
0.2-0.3	4894
0.3-0.4	9013
0.4-0.5	16004
0.5-0.6	7466
0.6-0.7	3309
0.7-0.8	500
0.8-0.85	22
0.85-0.9	7
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC472009
0.9639	High Similarity	NPC472007
0.8652	High Similarity	NPC265856
0.8652	High Similarity	NPC166554
0.8495	Intermediate Similarity	NPC20066
0.8404	Intermediate Similarity	NPC300584
0.8315	Intermediate Similarity	NPC471738
0.8265	Intermediate Similarity	NPC469852
0.8242	Intermediate Similarity	NPC471399
0.8111	Intermediate Similarity	NPC179659
0.8068	Intermediate Similarity	NPC477784
0.8068	Intermediate Similarity	NPC477785
0.8068	Intermediate Similarity	NPC477786
0.8065	Intermediate Similarity	NPC469645
0.8065	Intermediate Similarity	NPC469692
0.8041	Intermediate Similarity	NPC133907
0.8041	Intermediate Similarity	NPC185141
0.8041	Intermediate Similarity	NPC469851
0.8041	Intermediate Similarity	NPC128733
0.8041	Intermediate Similarity	NPC46998
0.8041	Intermediate Similarity	NPC110443
0.7979	Intermediate Similarity	NPC121825
0.7978	Intermediate Similarity	NPC70424
0.7978	Intermediate Similarity	NPC243618
0.7959	Intermediate Similarity	NPC39996
0.7879	Intermediate Similarity	NPC472755
0.7857	Intermediate Similarity	NPC474742
0.7857	Intermediate Similarity	NPC472753
0.7849	Intermediate Similarity	NPC477684
0.7849	Intermediate Similarity	NPC469464
0.7841	Intermediate Similarity	NPC275766
0.7835	Intermediate Similarity	NPC35717
0.7835	Intermediate Similarity	NPC306908
0.7822	Intermediate Similarity	NPC469853
0.7816	Intermediate Similarity	NPC471740
0.7812	Intermediate Similarity	NPC93271
0.7812	Intermediate Similarity	NPC135576
0.7791	Intermediate Similarity	NPC473536
0.7789	Intermediate Similarity	NPC477241
0.7789	Intermediate Similarity	NPC469632
0.7788	Intermediate Similarity	NPC66108
0.7778	Intermediate Similarity	NPC149371
0.7778	Intermediate Similarity	NPC472754
0.7766	Intermediate Similarity	NPC146852
0.7732	Intermediate Similarity	NPC239895
0.7727	Intermediate Similarity	NPC233377
0.7717	Intermediate Similarity	NPC471739
0.7717	Intermediate Similarity	NPC23622
0.7701	Intermediate Similarity	NPC478122
0.77	Intermediate Similarity	NPC475871
0.77	Intermediate Similarity	NPC475945
0.7692	Intermediate Similarity	NPC68303
0.7692	Intermediate Similarity	NPC307126
0.7692	Intermediate Similarity	NPC77971
0.7692	Intermediate Similarity	NPC187529
0.7684	Intermediate Similarity	NPC61275
0.7677	Intermediate Similarity	NPC47880
0.767	Intermediate Similarity	NPC38154
0.7667	Intermediate Similarity	NPC185256
0.766	Intermediate Similarity	NPC313670
0.7647	Intermediate Similarity	NPC160540
0.764	Intermediate Similarity	NPC286229
0.7634	Intermediate Similarity	NPC228415
0.7634	Intermediate Similarity	NPC87189
0.7624	Intermediate Similarity	NPC474741
0.7609	Intermediate Similarity	NPC261721
0.76	Intermediate Similarity	NPC474747
0.7582	Intermediate Similarity	NPC72464
0.7582	Intermediate Similarity	NPC9868
0.7579	Intermediate Similarity	NPC300312
0.7579	Intermediate Similarity	NPC111114
0.7579	Intermediate Similarity	NPC261607
0.7579	Intermediate Similarity	NPC475441
0.7558	Intermediate Similarity	NPC60718
0.7556	Intermediate Similarity	NPC85772
0.7556	Intermediate Similarity	NPC474252
0.7556	Intermediate Similarity	NPC475690
0.7553	Intermediate Similarity	NPC83423
0.7551	Intermediate Similarity	NPC40812
0.7549	Intermediate Similarity	NPC472749
0.7549	Intermediate Similarity	NPC472751
0.7528	Intermediate Similarity	NPC47653
0.7528	Intermediate Similarity	NPC103634
0.7527	Intermediate Similarity	NPC86005
0.7526	Intermediate Similarity	NPC91408
0.7525	Intermediate Similarity	NPC475873
0.7525	Intermediate Similarity	NPC104161
0.7525	Intermediate Similarity	NPC469980
0.7525	Intermediate Similarity	NPC118902
0.7525	Intermediate Similarity	NPC472747
0.7525	Intermediate Similarity	NPC472750
0.75	Intermediate Similarity	NPC288240
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC273579
0.75	Intermediate Similarity	NPC164598
0.75	Intermediate Similarity	NPC231739
0.75	Intermediate Similarity	NPC295204
0.75	Intermediate Similarity	NPC474339
0.75	Intermediate Similarity	NPC162205
0.75	Intermediate Similarity	NPC475912
0.75	Intermediate Similarity	NPC11804
0.7475	Intermediate Similarity	NPC278008
0.7475	Intermediate Similarity	NPC187761
0.7475	Intermediate Similarity	NPC471144
0.7475	Intermediate Similarity	NPC83895
0.7474	Intermediate Similarity	NPC316228
0.7474	Intermediate Similarity	NPC474761
0.7474	Intermediate Similarity	NPC476004
0.7473	Intermediate Similarity	NPC161045
0.7451	Intermediate Similarity	NPC472756
0.7451	Intermediate Similarity	NPC100487
0.7451	Intermediate Similarity	NPC472748
0.7449	Intermediate Similarity	NPC472733
0.7449	Intermediate Similarity	NPC184065
0.7449	Intermediate Similarity	NPC472734
0.7447	Intermediate Similarity	NPC469631
0.7447	Intermediate Similarity	NPC469628
0.7447	Intermediate Similarity	NPC471047
0.7447	Intermediate Similarity	NPC469653
0.7447	Intermediate Similarity	NPC53454
0.7447	Intermediate Similarity	NPC475902
0.7447	Intermediate Similarity	NPC153805
0.7447	Intermediate Similarity	NPC475906
0.7423	Intermediate Similarity	NPC469819
0.7423	Intermediate Similarity	NPC65829
0.7423	Intermediate Similarity	NPC114162
0.7419	Intermediate Similarity	NPC469483
0.7419	Intermediate Similarity	NPC196381
0.74	Intermediate Similarity	NPC288876
0.74	Intermediate Similarity	NPC174314
0.7396	Intermediate Similarity	NPC45579
0.7396	Intermediate Similarity	NPC32552
0.7396	Intermediate Similarity	NPC472705
0.7396	Intermediate Similarity	NPC166110
0.7391	Intermediate Similarity	NPC295799
0.7391	Intermediate Similarity	NPC474251
0.7391	Intermediate Similarity	NPC31086
0.7381	Intermediate Similarity	NPC94488
0.7374	Intermediate Similarity	NPC472731
0.7374	Intermediate Similarity	NPC472732
0.7374	Intermediate Similarity	NPC53844
0.7374	Intermediate Similarity	NPC471694
0.7368	Intermediate Similarity	NPC95364
0.7368	Intermediate Similarity	NPC280833
0.7368	Intermediate Similarity	NPC142159
0.7363	Intermediate Similarity	NPC474291
0.7358	Intermediate Similarity	NPC317107
0.7356	Intermediate Similarity	NPC199445
0.7347	Intermediate Similarity	NPC14961
0.7347	Intermediate Similarity	NPC471698
0.7347	Intermediate Similarity	NPC36954
0.7347	Intermediate Similarity	NPC475659
0.7347	Intermediate Similarity	NPC270013
0.734	Intermediate Similarity	NPC72513
0.734	Intermediate Similarity	NPC300779
0.734	Intermediate Similarity	NPC197333
0.734	Intermediate Similarity	NPC477959
0.7333	Intermediate Similarity	NPC91332
0.7333	Intermediate Similarity	NPC470945
0.7333	Intermediate Similarity	NPC162741
0.7333	Intermediate Similarity	NPC472948
0.7333	Intermediate Similarity	NPC471400
0.7333	Intermediate Similarity	NPC470947
0.7333	Intermediate Similarity	NPC470946
0.7327	Intermediate Similarity	NPC201718
0.7327	Intermediate Similarity	NPC476270
0.732	Intermediate Similarity	NPC475302
0.732	Intermediate Similarity	NPC248193
0.732	Intermediate Similarity	NPC476300
0.7312	Intermediate Similarity	NPC21469
0.7312	Intermediate Similarity	NPC471223
0.7312	Intermediate Similarity	NPC137033
0.7312	Intermediate Similarity	NPC125290
0.7312	Intermediate Similarity	NPC470177
0.7312	Intermediate Similarity	NPC67081
0.7312	Intermediate Similarity	NPC307112
0.7308	Intermediate Similarity	NPC266514
0.7308	Intermediate Similarity	NPC477513
0.7303	Intermediate Similarity	NPC121200
0.73	Intermediate Similarity	NPC472730
0.73	Intermediate Similarity	NPC153776
0.73	Intermediate Similarity	NPC308567
0.73	Intermediate Similarity	NPC177680
0.73	Intermediate Similarity	NPC255592
0.73	Intermediate Similarity	NPC261377
0.73	Intermediate Similarity	NPC161855
0.73	Intermediate Similarity	NPC472729
0.7294	Intermediate Similarity	NPC69462
0.7294	Intermediate Similarity	NPC477455
0.7292	Intermediate Similarity	NPC131864
0.7292	Intermediate Similarity	NPC474232
0.7292	Intermediate Similarity	NPC51004
0.7292	Intermediate Similarity	NPC77337
0.7292	Intermediate Similarity	NPC475879
0.729	Intermediate Similarity	NPC317687
0.7283	Intermediate Similarity	NPC258985
0.7282	Intermediate Similarity	NPC220964
0.7282	Intermediate Similarity	NPC475676
0.7282	Intermediate Similarity	NPC13385
0.7273	Intermediate Similarity	NPC251310

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 NPC472008 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1870
0.2-0.3	3646
0.3-0.4	2208
0.4-0.5	850
0.5-0.6	315
0.6-0.7	64
0.7-0.8	7
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
0.7791	Intermediate Similarity	NPD4756	Discovery
0.7579	Intermediate Similarity	NPD7983	Approved
0.732	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD46	Approved
0.7292	Intermediate Similarity	NPD6698	Approved
0.7283	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD6110	Phase 1
0.7071	Intermediate Similarity	NPD5282	Discontinued
0.7053	Intermediate Similarity	NPD5786	Approved
0.7024	Intermediate Similarity	NPD3704	Approved
0.7024	Intermediate Similarity	NPD7331	Phase 2
0.701	Intermediate Similarity	NPD6101	Approved
0.701	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5363	Approved
0.6931	Remote Similarity	NPD7839	Suspended
0.6869	Remote Similarity	NPD6411	Approved
0.6867	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4270	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6789	Remote Similarity	NPD6371	Approved
0.6768	Remote Similarity	NPD5785	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD6435	Approved
0.6628	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4252	Approved
0.6588	Remote Similarity	NPD3197	Phase 1
0.6574	Remote Similarity	NPD5739	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6552	Remote Similarity	NPD6319	Approved
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD6083	Phase 2
0.6518	Remote Similarity	NPD6053	Discontinued
0.6518	Remote Similarity	NPD8297	Approved
0.6514	Remote Similarity	NPD5697	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6512	Remote Similarity	NPD7341	Phase 2
0.6476	Remote Similarity	NPD5696	Approved
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6455	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4695	Discontinued
0.6421	Remote Similarity	NPD5368	Approved
0.6421	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6372	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4249	Approved
0.6356	Remote Similarity	NPD8516	Approved
0.6356	Remote Similarity	NPD8517	Approved
0.6356	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD8513	Phase 3
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD7102	Approved
0.6327	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4632	Approved
0.6306	Remote Similarity	NPD6011	Approved
0.6303	Remote Similarity	NPD8080	Discontinued
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.6296	Remote Similarity	NPD5211	Phase 2
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6263	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8328	Phase 3
0.6238	Remote Similarity	NPD6672	Approved
0.6238	Remote Similarity	NPD5737	Approved
0.6237	Remote Similarity	NPD8039	Approved
0.6228	Remote Similarity	NPD6882	Approved
0.6226	Remote Similarity	NPD4755	Approved
0.6214	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7637	Suspended
0.6211	Remote Similarity	NPD4268	Approved
0.6211	Remote Similarity	NPD4271	Approved
0.6204	Remote Similarity	NPD5344	Discontinued
0.62	Remote Similarity	NPD6422	Discontinued
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD4634	Approved
0.6182	Remote Similarity	NPD5141	Approved
0.618	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4753	Phase 2
0.6176	Remote Similarity	NPD5370	Suspended
0.6176	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6059	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6122	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5209	Approved
0.6116	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6111	Remote Similarity	NPD4700	Approved
0.61	Remote Similarity	NPD1694	Approved
0.6098	Remote Similarity	NPD8293	Discontinued
0.6098	Remote Similarity	NPD7078	Approved
0.6098	Remote Similarity	NPD8074	Phase 3
0.6083	Remote Similarity	NPD6015	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7902	Approved
0.6068	Remote Similarity	NPD6274	Approved
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD7515	Phase 2
0.6058	Remote Similarity	NPD5693	Phase 1
0.6053	Remote Similarity	NPD2067	Discontinued
0.6048	Remote Similarity	NPD7736	Approved
0.604	Remote Similarity	NPD5330	Approved
0.604	Remote Similarity	NPD7334	Approved
0.604	Remote Similarity	NPD6409	Approved
0.604	Remote Similarity	NPD7521	Approved
0.604	Remote Similarity	NPD7146	Approved
0.604	Remote Similarity	NPD6684	Approved
0.604	Remote Similarity	NPD5279	Phase 3
0.6033	Remote Similarity	NPD6370	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD6904	Approved
0.6019	Remote Similarity	NPD6673	Approved
0.6019	Remote Similarity	NPD6080	Approved
0.6017	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD6109	Phase 1
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7829	Approved
0.5981	Remote Similarity	NPD5221	Approved
0.5981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4697	Phase 3
0.5981	Remote Similarity	NPD5222	Approved
0.598	Remote Similarity	NPD3573	Approved
0.5966	Remote Similarity	NPD7641	Discontinued
0.5965	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6648	Approved
0.5962	Remote Similarity	NPD5692	Phase 3
0.595	Remote Similarity	NPD8444	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.5946	Remote Similarity	NPD5175	Approved
0.5946	Remote Similarity	NPD5174	Approved
0.5935	Remote Similarity	NPD8342	Approved
0.5935	Remote Similarity	NPD8340	Approved
0.5935	Remote Similarity	NPD8341	Approved
0.5935	Remote Similarity	NPD8299	Approved
0.5932	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6412	Phase 2
0.5926	Remote Similarity	NPD5173	Approved
0.5922	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6903	Approved
0.5917	Remote Similarity	NPD7100	Approved
0.5917	Remote Similarity	NPD7101	Approved
0.5909	Remote Similarity	NPD5223	Approved
0.5906	Remote Similarity	NPD7260	Phase 2
0.5905	Remote Similarity	NPD5694	Approved
0.5905	Remote Similarity	NPD6050	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5888	Remote Similarity	NPD4629	Approved
0.5882	Remote Similarity	NPD4519	Discontinued
0.5882	Remote Similarity	NPD7500	Approved
0.5882	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4623	Approved
0.5882	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6317	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