NPASS Compound

Structure

NPC472983 OpenBabel07101718292D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 20 1 1 0 0 0 15 22 2 0 0 0 0 16 18 1 0 0 0 0 16 23 1 6 0 0 0 17 19 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	364.615
LogP:	2.554
LogD:	2.118
LogS:	-2.505
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	4.566
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	2.5722270947881043e-05
Pgp-inhibitor:	0.497
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.95
Plasma Protein Binding (PPB):	58.99658966064453%
Volume Distribution (VD):	0.736
Pgp-substrate:	37.864498138427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.224
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.243
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	9.345
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.683
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.814
Carcinogencity:	0.712
Eye Corrosion:	0.587
Eye Irritation:	0.182
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC472983

Natural Product ID:	NPC472983
*Common Name:**	GZAWIMMRLPNFME-SVEODPQUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GZAWIMMRLPNFME-SVEODPQUSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-12(2)15(22)7-6-14-13(11-21)10-16(23)18-19(3,4)17(24)8-9-20(14,18)5/h10-12,14,16-18,23-24H,6-9H2,1-5H3/t14-,16-,17-,18-,20+/m1/s1
SMILES:	O=CC1=C[C@@H](O)[C@H]2[C@@]([C@@H]1CCC(=O)C(C)C)(C)CC[C@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594347
PubChem CID:	n.a.
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
NPO32900	chloranthus sessilifolius	Species	Chloranthaceae	Eukaryota	Whole plants	Fengqi Mountains, Sichuan Province, China	2012-Aug	PMID[26126961]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[552987]

☑ 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 NPC472983 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	1158
0.2-0.3	4332
0.3-0.4	10127
0.4-0.5	12971
0.5-0.6	7196
0.6-0.7	4843
0.7-0.8	1690
0.8-0.85	155
0.85-0.9	40
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8876	High Similarity	NPC472978
0.8864	High Similarity	NPC472973
0.8795	High Similarity	NPC308038
0.8764	High Similarity	NPC134321
0.8764	High Similarity	NPC191684
0.875	High Similarity	NPC104560
0.875	High Similarity	NPC473229
0.875	High Similarity	NPC206060
0.8736	High Similarity	NPC472974
0.8736	High Similarity	NPC472986
0.8736	High Similarity	NPC473226
0.8736	High Similarity	NPC472985
0.8706	High Similarity	NPC93590
0.869	High Similarity	NPC472301
0.869	High Similarity	NPC471514
0.869	High Similarity	NPC172013
0.8681	High Similarity	NPC299100
0.8681	High Similarity	NPC472977
0.8681	High Similarity	NPC472976
0.8667	High Similarity	NPC473998
0.8667	High Similarity	NPC99380
0.8652	High Similarity	NPC309603
0.8652	High Similarity	NPC473999
0.8621	High Similarity	NPC476426
0.8587	High Similarity	NPC180950
0.8571	High Similarity	NPC152061
0.8571	High Similarity	NPC69454
0.8571	High Similarity	NPC281138
0.8556	High Similarity	NPC128672
0.8556	High Similarity	NPC48010
0.8554	High Similarity	NPC197659
0.8539	High Similarity	NPC474925
0.8523	High Similarity	NPC470955
0.8523	High Similarity	NPC194417
0.8511	High Similarity	NPC478056
0.8506	High Similarity	NPC476412
0.8506	High Similarity	NPC470812
0.8495	Intermediate Similarity	NPC301534
0.8495	Intermediate Similarity	NPC5532
0.8495	Intermediate Similarity	NPC117133
0.8495	Intermediate Similarity	NPC61369
0.8495	Intermediate Similarity	NPC469545
0.8495	Intermediate Similarity	NPC249954
0.8495	Intermediate Similarity	NPC250757
0.8478	Intermediate Similarity	NPC474690
0.8478	Intermediate Similarity	NPC196227
0.8478	Intermediate Similarity	NPC8993
0.8471	Intermediate Similarity	NPC104120
0.8471	Intermediate Similarity	NPC157895
0.8471	Intermediate Similarity	NPC148685
0.8462	Intermediate Similarity	NPC73457
0.8462	Intermediate Similarity	NPC475806
0.8462	Intermediate Similarity	NPC116726
0.8462	Intermediate Similarity	NPC472975
0.8462	Intermediate Similarity	NPC172101
0.8462	Intermediate Similarity	NPC63748
0.8462	Intermediate Similarity	NPC233116
0.8452	Intermediate Similarity	NPC475994
0.8452	Intermediate Similarity	NPC80088
0.8452	Intermediate Similarity	NPC253561
0.8452	Intermediate Similarity	NPC62336
0.8444	Intermediate Similarity	NPC472970
0.8444	Intermediate Similarity	NPC472971
0.8434	Intermediate Similarity	NPC263582
0.8421	Intermediate Similarity	NPC476274
0.8421	Intermediate Similarity	NPC154072
0.8409	Intermediate Similarity	NPC470574
0.8404	Intermediate Similarity	NPC253826
0.8391	Intermediate Similarity	NPC297398
0.8391	Intermediate Similarity	NPC64600
0.8391	Intermediate Similarity	NPC105173
0.8387	Intermediate Similarity	NPC476245
0.8387	Intermediate Similarity	NPC259286
0.8387	Intermediate Similarity	NPC271195
0.8372	Intermediate Similarity	NPC226068
0.837	Intermediate Similarity	NPC475255
0.837	Intermediate Similarity	NPC472930
0.837	Intermediate Similarity	NPC109305
0.8353	Intermediate Similarity	NPC470429
0.8352	Intermediate Similarity	NPC183283
0.8352	Intermediate Similarity	NPC85173
0.8352	Intermediate Similarity	NPC473099
0.8333	Intermediate Similarity	NPC203403
0.8333	Intermediate Similarity	NPC471722
0.8333	Intermediate Similarity	NPC266193
0.8333	Intermediate Similarity	NPC48107
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC257666
0.8333	Intermediate Similarity	NPC470428
0.8333	Intermediate Similarity	NPC471793
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC472802
0.8333	Intermediate Similarity	NPC74995
0.8333	Intermediate Similarity	NPC471791
0.8333	Intermediate Similarity	NPC476223
0.8333	Intermediate Similarity	NPC115862
0.8316	Intermediate Similarity	NPC103051
0.8315	Intermediate Similarity	NPC198761
0.8315	Intermediate Similarity	NPC72133
0.8315	Intermediate Similarity	NPC477579
0.8315	Intermediate Similarity	NPC95594
0.8315	Intermediate Similarity	NPC322159
0.8315	Intermediate Similarity	NPC235341
0.8315	Intermediate Similarity	NPC94755
0.8315	Intermediate Similarity	NPC158393
0.8298	Intermediate Similarity	NPC472941
0.8298	Intermediate Similarity	NPC456
0.8298	Intermediate Similarity	NPC473158
0.8295	Intermediate Similarity	NPC40687
0.828	Intermediate Similarity	NPC103527
0.828	Intermediate Similarity	NPC111015
0.828	Intermediate Similarity	NPC292793
0.828	Intermediate Similarity	NPC23170
0.8276	Intermediate Similarity	NPC48362
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC145067
0.8261	Intermediate Similarity	NPC233455
0.8261	Intermediate Similarity	NPC4036
0.8261	Intermediate Similarity	NPC158030
0.8261	Intermediate Similarity	NPC65120
0.8256	Intermediate Similarity	NPC306095
0.8256	Intermediate Similarity	NPC2482
0.8247	Intermediate Similarity	NPC473424
0.8247	Intermediate Similarity	NPC136289
0.8247	Intermediate Similarity	NPC293753
0.8242	Intermediate Similarity	NPC86319
0.8242	Intermediate Similarity	NPC473100
0.8242	Intermediate Similarity	NPC31985
0.8242	Intermediate Similarity	NPC123912
0.8242	Intermediate Similarity	NPC1015
0.8242	Intermediate Similarity	NPC119416
0.8242	Intermediate Similarity	NPC314727
0.8242	Intermediate Similarity	NPC275740
0.8242	Intermediate Similarity	NPC184663
0.8242	Intermediate Similarity	NPC214387
0.8235	Intermediate Similarity	NPC476949
0.8235	Intermediate Similarity	NPC471409
0.8235	Intermediate Similarity	NPC297996
0.8235	Intermediate Similarity	NPC275494
0.8229	Intermediate Similarity	NPC470074
0.8222	Intermediate Similarity	NPC475740
0.8222	Intermediate Similarity	NPC141292
0.8214	Intermediate Similarity	NPC472305
0.8211	Intermediate Similarity	NPC474785
0.8211	Intermediate Similarity	NPC474938
0.8211	Intermediate Similarity	NPC320306
0.8202	Intermediate Similarity	NPC471224
0.8202	Intermediate Similarity	NPC474083
0.8202	Intermediate Similarity	NPC197823
0.8202	Intermediate Similarity	NPC133954
0.8202	Intermediate Similarity	NPC274724
0.8202	Intermediate Similarity	NPC109528
0.8202	Intermediate Similarity	NPC70685
0.8191	Intermediate Similarity	NPC139570
0.8191	Intermediate Similarity	NPC53565
0.8191	Intermediate Similarity	NPC134067
0.8182	Intermediate Similarity	NPC251475
0.8182	Intermediate Similarity	NPC307258
0.8182	Intermediate Similarity	NPC169941
0.8172	Intermediate Similarity	NPC295643
0.8172	Intermediate Similarity	NPC272075
0.8172	Intermediate Similarity	NPC474736
0.8172	Intermediate Similarity	NPC214756
0.8163	Intermediate Similarity	NPC95899
0.8163	Intermediate Similarity	NPC478057
0.8161	Intermediate Similarity	NPC473217
0.8161	Intermediate Similarity	NPC473420
0.8161	Intermediate Similarity	NPC116797
0.8161	Intermediate Similarity	NPC6663
0.8161	Intermediate Similarity	NPC90055
0.8161	Intermediate Similarity	NPC119229
0.8152	Intermediate Similarity	NPC126993
0.8152	Intermediate Similarity	NPC477149
0.8152	Intermediate Similarity	NPC230332
0.8152	Intermediate Similarity	NPC477147
0.8144	Intermediate Similarity	NPC472637
0.8144	Intermediate Similarity	NPC81530
0.8144	Intermediate Similarity	NPC282524
0.814	Intermediate Similarity	NPC170394
0.8132	Intermediate Similarity	NPC471724
0.8132	Intermediate Similarity	NPC310752
0.8132	Intermediate Similarity	NPC131470
0.8132	Intermediate Similarity	NPC158778
0.8132	Intermediate Similarity	NPC292491
0.8132	Intermediate Similarity	NPC328539
0.8132	Intermediate Similarity	NPC143767
0.8125	Intermediate Similarity	NPC316598
0.8125	Intermediate Similarity	NPC57079
0.8125	Intermediate Similarity	NPC108368
0.8125	Intermediate Similarity	NPC471966
0.8125	Intermediate Similarity	NPC194196
0.8118	Intermediate Similarity	NPC34110
0.8111	Intermediate Similarity	NPC474733
0.8111	Intermediate Similarity	NPC82979
0.8111	Intermediate Similarity	NPC145879
0.8111	Intermediate Similarity	NPC474778
0.8111	Intermediate Similarity	NPC34190
0.8111	Intermediate Similarity	NPC179591
0.8111	Intermediate Similarity	NPC73038
0.8111	Intermediate Similarity	NPC474732

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 NPC472983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1610
0.2-0.3	3726
0.3-0.4	2449
0.4-0.5	743
0.5-0.6	214
0.6-0.7	193
0.7-0.8	51
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
0.8315	Intermediate Similarity	NPD3618	Phase 1
0.8261	Intermediate Similarity	NPD7515	Phase 2
0.8261	Intermediate Similarity	NPD6079	Approved
0.8242	Intermediate Similarity	NPD5328	Approved
0.8105	Intermediate Similarity	NPD4697	Phase 3
0.8061	Intermediate Similarity	NPD5211	Phase 2
0.7979	Intermediate Similarity	NPD4202	Approved
0.7917	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5221	Approved
0.7917	Intermediate Similarity	NPD5222	Approved
0.79	Intermediate Similarity	NPD5141	Approved
0.7895	Intermediate Similarity	NPD7748	Approved
0.7889	Intermediate Similarity	NPD3665	Phase 1
0.7889	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD3666	Approved
0.7889	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD3667	Approved
0.7857	Intermediate Similarity	NPD4696	Approved
0.7857	Intermediate Similarity	NPD5285	Approved
0.7857	Intermediate Similarity	NPD5286	Approved
0.7835	Intermediate Similarity	NPD5173	Approved
0.7835	Intermediate Similarity	NPD7902	Approved
0.7835	Intermediate Similarity	NPD4755	Approved
0.7778	Intermediate Similarity	NPD5223	Approved
0.77	Intermediate Similarity	NPD5225	Approved
0.77	Intermediate Similarity	NPD4633	Approved
0.77	Intermediate Similarity	NPD5226	Approved
0.77	Intermediate Similarity	NPD5224	Approved
0.7677	Intermediate Similarity	NPD4700	Approved
0.764	Intermediate Similarity	NPD4695	Discontinued
0.7624	Intermediate Similarity	NPD5175	Approved
0.7624	Intermediate Similarity	NPD5174	Approved
0.7527	Intermediate Similarity	NPD4623	Approved
0.7527	Intermediate Similarity	NPD4519	Discontinued
0.7527	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5279	Phase 3
0.7526	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD5739	Approved
0.7476	Intermediate Similarity	NPD6675	Approved
0.7476	Intermediate Similarity	NPD7128	Approved
0.7476	Intermediate Similarity	NPD6402	Approved
0.7474	Intermediate Similarity	NPD4753	Phase 2
0.7451	Intermediate Similarity	NPD4754	Approved
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7404	Intermediate Similarity	NPD5697	Approved
0.74	Intermediate Similarity	NPD7638	Approved
0.7358	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7102	Approved
0.7358	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD4729	Approved
0.7333	Intermediate Similarity	NPD5128	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7312	Intermediate Similarity	NPD3668	Phase 3
0.7308	Intermediate Similarity	NPD4768	Approved
0.7308	Intermediate Similarity	NPD4767	Approved
0.729	Intermediate Similarity	NPD6869	Approved
0.729	Intermediate Similarity	NPD6650	Approved
0.729	Intermediate Similarity	NPD6617	Approved
0.729	Intermediate Similarity	NPD6649	Approved
0.729	Intermediate Similarity	NPD6847	Approved
0.729	Intermediate Similarity	NPD8130	Phase 1
0.7283	Intermediate Similarity	NPD4221	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD4629	Approved
0.7264	Intermediate Similarity	NPD6372	Approved
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6373	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7253	Intermediate Similarity	NPD7525	Registered
0.7253	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5701	Approved
0.7234	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD1696	Phase 3
0.7234	Intermediate Similarity	NPD5329	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6882	Approved
0.7196	Intermediate Similarity	NPD5249	Phase 3
0.7196	Intermediate Similarity	NPD5248	Approved
0.7196	Intermediate Similarity	NPD5247	Approved
0.7196	Intermediate Similarity	NPD5250	Approved
0.7196	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5135	Approved
0.7196	Intermediate Similarity	NPD4634	Approved
0.7196	Intermediate Similarity	NPD5251	Approved
0.7196	Intermediate Similarity	NPD5169	Approved
0.717	Intermediate Similarity	NPD5168	Approved
0.7158	Intermediate Similarity	NPD7146	Approved
0.7158	Intermediate Similarity	NPD7521	Approved
0.7158	Intermediate Similarity	NPD7334	Approved
0.7158	Intermediate Similarity	NPD5690	Phase 2
0.7158	Intermediate Similarity	NPD6409	Approved
0.7158	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.713	Intermediate Similarity	NPD5217	Approved
0.713	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5216	Approved
0.713	Intermediate Similarity	NPD5127	Approved
0.713	Intermediate Similarity	NPD5215	Approved
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7128	Intermediate Similarity	NPD4197	Approved
0.7097	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3573	Approved
0.7079	Intermediate Similarity	NPD8264	Approved
0.7053	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD3617	Approved
0.7033	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4788	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD6903	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.701	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4632	Approved
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD5280	Approved
0.6979	Remote Similarity	NPD4694	Approved
0.6979	Remote Similarity	NPD4690	Approved
0.6979	Remote Similarity	NPD4689	Approved
0.6979	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6939	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5167	Approved
0.6931	Remote Similarity	NPD5695	Phase 3
0.6916	Remote Similarity	NPD6412	Phase 2
0.6903	Remote Similarity	NPD6335	Approved
0.69	Remote Similarity	NPD5779	Approved
0.69	Remote Similarity	NPD5778	Approved
0.6889	Remote Similarity	NPD7339	Approved
0.6889	Remote Similarity	NPD6942	Approved
0.6875	Remote Similarity	NPD6274	Approved
0.6875	Remote Similarity	NPD6868	Approved
0.6875	Remote Similarity	NPD5363	Approved
0.6869	Remote Similarity	NPD5785	Approved
0.6857	Remote Similarity	NPD7632	Discontinued
0.6852	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7101	Approved
0.6818	Remote Similarity	NPD4691	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6813	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD8035	Phase 2
0.68	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD4195	Approved
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD7331	Phase 2
0.6731	Remote Similarity	NPD5696	Approved
0.6731	Remote Similarity	NPD5290	Discontinued
0.6705	Remote Similarity	NPD4137	Phase 3
0.6699	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6059	Approved
0.6638	Remote Similarity	NPD6319	Approved
0.6629	Remote Similarity	NPD4747	Approved
0.6628	Remote Similarity	NPD7341	Phase 2
0.661	Remote Similarity	NPD7604	Phase 2
0.66	Remote Similarity	NPD6080	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6673	Approved
0.66	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD6904	Approved
0.6593	Remote Similarity	NPD5733	Approved
0.6593	Remote Similarity	NPD4058	Approved
0.6581	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6015	Approved
0.6581	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD6908	Approved
0.6581	Remote Similarity	NPD6016	Approved
0.6581	Remote Similarity	NPD6909	Approved
0.6577	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4269	Approved
0.6562	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD6116	Phase 1
0.6556	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4808	Clinical (unspecified phase)

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