NPASS Compound

Structure

NPC476458 OpenBabel07101718192D 23 27 0 0 1 0 0 0 0 0999 V2000 4.1886 -1.0087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0340 2.1637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3086 -0.1777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2525 0.2607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7113 -1.3520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2888 1.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3527 0.7695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2077 0.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2137 -0.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9178 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6195 -0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2376 -0.6997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4285 -1.2874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6707 0.9528 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9285 0.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4319 0.5762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0174 1.1650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3104 -0.1179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9285 0.2514 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6814 0.2327 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5163 1.0604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4318 0.5612 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 1 12 2 0 0 0 0 3 18 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 20 1 0 0 0 0 9 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 5 1 6 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 2 1 1 0 0 0 18 19 1 6 0 0 0 19 10 1 1 0 0 0 20 18 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	330.155
LogP:	2.628
LogD:	2.008
LogS:	-5.072
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	6.214
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.999
MDCK Permeability:	2.973797745653428e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	93.56066131591797%
Volume Distribution (VD):	1.082
Pgp-substrate:	4.042758464813232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.862
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	5.584
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.47
Carcinogencity:	0.765
Eye Corrosion:	0.01
Eye Irritation:	0.057
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC476458

Natural Product ID:	NPC476458
*Common Name:**	JZONYWULSJTTAI-HGKZMHGGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JZONYWULSJTTAI-HGKZMHGGSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-12-13-5-9-18(3)19(11-13,15(12)21)10-6-14-17(2)7-4-8-20(14,18)23-16(17)22/h13-14H,1,4-11H2,2-3H3/t13-,14?,17-,18+,19+,20+/m1/s1
SMILES:	C=C1[C@@H]2CC[C@]3([C@](C1=O)(C2)CCC1[C@]23CCC[C@]1(C(=O)O2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL69315
PubChem CID:	44308974
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO26247	Parinari capensis	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12127529]
NPO26247	Parinari capensis	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO26247	Parinari capensis	Species	Chrysobalanaceae	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
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1.57	ug.mL-1	PMID[505270]
NPT27	Others	Unspecified		IC50	=	3.01	ug.mL-1	PMID[505270]

☑ 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 NPC476458 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	240
0.1-0.2	1983
0.2-0.3	8905
0.3-0.4	14469
0.4-0.5	6036
0.5-0.6	6657
0.6-0.7	3736
0.7-0.8	634
0.8-0.85	26
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC258153
0.8861	High Similarity	NPC471475
0.8795	High Similarity	NPC471042
0.8625	High Similarity	NPC118987
0.8608	High Similarity	NPC212661
0.8608	High Similarity	NPC471035
0.8537	High Similarity	NPC476935
0.8523	High Similarity	NPC224410
0.8523	High Similarity	NPC100257
0.8519	High Similarity	NPC170038
0.8488	Intermediate Similarity	NPC11611
0.8427	Intermediate Similarity	NPC471624
0.8427	Intermediate Similarity	NPC197158
0.8415	Intermediate Similarity	NPC232625
0.8333	Intermediate Similarity	NPC279241
0.8295	Intermediate Similarity	NPC250753
0.8276	Intermediate Similarity	NPC471043
0.8272	Intermediate Similarity	NPC63020
0.825	Intermediate Similarity	NPC92489
0.8235	Intermediate Similarity	NPC470223
0.8214	Intermediate Similarity	NPC471037
0.8205	Intermediate Similarity	NPC197701
0.8202	Intermediate Similarity	NPC294263
0.8202	Intermediate Similarity	NPC475700
0.8158	Intermediate Similarity	NPC469868
0.8148	Intermediate Similarity	NPC66105
0.8118	Intermediate Similarity	NPC475509
0.8101	Intermediate Similarity	NPC161187
0.8101	Intermediate Similarity	NPC330659
0.8101	Intermediate Similarity	NPC244708
0.8095	Intermediate Similarity	NPC226988
0.809	Intermediate Similarity	NPC470230
0.8023	Intermediate Similarity	NPC98270
0.8022	Intermediate Similarity	NPC210214
0.8022	Intermediate Similarity	NPC98639
0.8022	Intermediate Similarity	NPC280877
0.8	Intermediate Similarity	NPC472740
0.8	Intermediate Similarity	NPC118800
0.7976	Intermediate Similarity	NPC475951
0.7955	Intermediate Similarity	NPC28227
0.7955	Intermediate Similarity	NPC474845
0.7952	Intermediate Similarity	NPC263951
0.7952	Intermediate Similarity	NPC192744
0.7935	Intermediate Similarity	NPC200054
0.7935	Intermediate Similarity	NPC104568
0.7935	Intermediate Similarity	NPC29410
0.7935	Intermediate Similarity	NPC13949
0.7931	Intermediate Similarity	NPC9231
0.7927	Intermediate Similarity	NPC106078
0.7927	Intermediate Similarity	NPC475932
0.7912	Intermediate Similarity	NPC47853
0.7912	Intermediate Similarity	NPC475118
0.7907	Intermediate Similarity	NPC219011
0.7907	Intermediate Similarity	NPC146683
0.7901	Intermediate Similarity	NPC39362
0.7895	Intermediate Similarity	NPC474768
0.7872	Intermediate Similarity	NPC267921
0.7865	Intermediate Similarity	NPC285982
0.7849	Intermediate Similarity	NPC10864
0.7841	Intermediate Similarity	NPC476932
0.7841	Intermediate Similarity	NPC30421
0.7841	Intermediate Similarity	NPC175293
0.7826	Intermediate Similarity	NPC470229
0.7826	Intermediate Similarity	NPC470232
0.7816	Intermediate Similarity	NPC102292
0.7805	Intermediate Similarity	NPC246445
0.7802	Intermediate Similarity	NPC470224
0.7792	Intermediate Similarity	NPC84562
0.7791	Intermediate Similarity	NPC194637
0.7791	Intermediate Similarity	NPC471036
0.7791	Intermediate Similarity	NPC291320
0.7791	Intermediate Similarity	NPC170862
0.7778	Intermediate Similarity	NPC76286
0.7766	Intermediate Similarity	NPC78427
0.7766	Intermediate Similarity	NPC20479
0.7766	Intermediate Similarity	NPC89099
0.7766	Intermediate Similarity	NPC471038
0.7766	Intermediate Similarity	NPC38296
0.7766	Intermediate Similarity	NPC98837
0.7766	Intermediate Similarity	NPC252295
0.7766	Intermediate Similarity	NPC28864
0.7766	Intermediate Similarity	NPC16911
0.7766	Intermediate Similarity	NPC162459
0.7766	Intermediate Similarity	NPC38471
0.7765	Intermediate Similarity	NPC209318
0.7765	Intermediate Similarity	NPC38642
0.7765	Intermediate Similarity	NPC223330
0.7765	Intermediate Similarity	NPC475665
0.7753	Intermediate Similarity	NPC56413
0.7753	Intermediate Similarity	NPC4309
0.7753	Intermediate Similarity	NPC474719
0.7742	Intermediate Similarity	NPC329910
0.7742	Intermediate Similarity	NPC307164
0.7727	Intermediate Similarity	NPC12774
0.7727	Intermediate Similarity	NPC85698
0.7717	Intermediate Similarity	NPC470385
0.7717	Intermediate Similarity	NPC472223
0.7717	Intermediate Similarity	NPC41649
0.7717	Intermediate Similarity	NPC472224
0.7717	Intermediate Similarity	NPC470386
0.7711	Intermediate Similarity	NPC68828
0.7711	Intermediate Similarity	NPC238227
0.7711	Intermediate Similarity	NPC472300
0.7701	Intermediate Similarity	NPC100391
0.7701	Intermediate Similarity	NPC470011
0.7692	Intermediate Similarity	NPC211403
0.7692	Intermediate Similarity	NPC476934
0.7692	Intermediate Similarity	NPC160506
0.7692	Intermediate Similarity	NPC198242
0.7684	Intermediate Similarity	NPC293866
0.7684	Intermediate Similarity	NPC287676
0.7674	Intermediate Similarity	NPC100297
0.7667	Intermediate Similarity	NPC305039
0.7667	Intermediate Similarity	NPC173042
0.7667	Intermediate Similarity	NPC473039
0.7667	Intermediate Similarity	NPC288699
0.766	Intermediate Similarity	NPC96839
0.766	Intermediate Similarity	NPC292133
0.766	Intermediate Similarity	NPC253586
0.766	Intermediate Similarity	NPC226986
0.7654	Intermediate Similarity	NPC472813
0.7647	Intermediate Similarity	NPC206735
0.764	Intermediate Similarity	NPC165895
0.764	Intermediate Similarity	NPC181103
0.764	Intermediate Similarity	NPC153604
0.764	Intermediate Similarity	NPC33768
0.764	Intermediate Similarity	NPC305029
0.764	Intermediate Similarity	NPC174619
0.7619	Intermediate Similarity	NPC321690
0.7619	Intermediate Similarity	NPC476810
0.7614	Intermediate Similarity	NPC471034
0.7614	Intermediate Similarity	NPC474971
0.7614	Intermediate Similarity	NPC264317
0.7614	Intermediate Similarity	NPC323765
0.7614	Intermediate Similarity	NPC76518
0.7614	Intermediate Similarity	NPC29447
0.7614	Intermediate Similarity	NPC294438
0.7614	Intermediate Similarity	NPC190704
0.7609	Intermediate Similarity	NPC474185
0.7604	Intermediate Similarity	NPC46848
0.7604	Intermediate Similarity	NPC289148
0.7604	Intermediate Similarity	NPC52899
0.7604	Intermediate Similarity	NPC163963
0.7604	Intermediate Similarity	NPC252614
0.759	Intermediate Similarity	NPC471046
0.759	Intermediate Similarity	NPC476601
0.759	Intermediate Similarity	NPC104806
0.759	Intermediate Similarity	NPC20466
0.7582	Intermediate Similarity	NPC474842
0.7582	Intermediate Similarity	NPC475965
0.7582	Intermediate Similarity	NPC475776
0.7582	Intermediate Similarity	NPC8062
0.7579	Intermediate Similarity	NPC473155
0.7579	Intermediate Similarity	NPC26270
0.7561	Intermediate Similarity	NPC38426
0.7558	Intermediate Similarity	NPC473217
0.7558	Intermediate Similarity	NPC58631
0.7558	Intermediate Similarity	NPC147066
0.7556	Intermediate Similarity	NPC48107
0.7556	Intermediate Similarity	NPC250687
0.7556	Intermediate Similarity	NPC215831
0.7556	Intermediate Similarity	NPC229407
0.7556	Intermediate Similarity	NPC254572
0.7556	Intermediate Similarity	NPC48824
0.7556	Intermediate Similarity	NPC472739
0.7553	Intermediate Similarity	NPC322063
0.7553	Intermediate Similarity	NPC470387
0.7529	Intermediate Similarity	NPC215843
0.7529	Intermediate Similarity	NPC47808
0.7529	Intermediate Similarity	NPC305835
0.7528	Intermediate Similarity	NPC185638
0.7528	Intermediate Similarity	NPC472505
0.7528	Intermediate Similarity	NPC2783
0.7528	Intermediate Similarity	NPC195640
0.7527	Intermediate Similarity	NPC56525
0.7527	Intermediate Similarity	NPC303863
0.7526	Intermediate Similarity	NPC275990
0.7526	Intermediate Similarity	NPC76866
0.7526	Intermediate Similarity	NPC304832
0.7526	Intermediate Similarity	NPC246736
0.7526	Intermediate Similarity	NPC214946
0.7526	Intermediate Similarity	NPC286519
0.7526	Intermediate Similarity	NPC88203
0.7526	Intermediate Similarity	NPC148628
0.75	Intermediate Similarity	NPC201406
0.75	Intermediate Similarity	NPC470906
0.75	Intermediate Similarity	NPC74685
0.75	Intermediate Similarity	NPC49420
0.75	Intermediate Similarity	NPC474482
0.75	Intermediate Similarity	NPC139566
0.75	Intermediate Similarity	NPC196197
0.75	Intermediate Similarity	NPC263974
0.75	Intermediate Similarity	NPC471901
0.75	Intermediate Similarity	NPC476303
0.75	Intermediate Similarity	NPC475745
0.75	Intermediate Similarity	NPC475416
0.75	Intermediate Similarity	NPC470388
0.75	Intermediate Similarity	NPC218301
0.75	Intermediate Similarity	NPC477857
0.75	Intermediate Similarity	NPC97505

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 NPC476458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	2309
0.2-0.3	4319
0.3-0.4	1558
0.4-0.5	350
0.5-0.6	170
0.6-0.7	177
0.7-0.8	37
0.8-0.85	1
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	NPD6001	Approved
0.8222	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD5207	Approved
0.7841	Intermediate Similarity	NPD3573	Approved
0.7753	Intermediate Similarity	NPD5208	Approved
0.7727	Intermediate Similarity	NPD6098	Approved
0.7692	Intermediate Similarity	NPD8035	Phase 2
0.7692	Intermediate Similarity	NPD8034	Phase 2
0.7667	Intermediate Similarity	NPD6904	Approved
0.7667	Intermediate Similarity	NPD6673	Approved
0.7667	Intermediate Similarity	NPD6080	Approved
0.7614	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4788	Approved
0.7556	Intermediate Similarity	NPD6672	Approved
0.7556	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6903	Approved
0.7556	Intermediate Similarity	NPD5737	Approved
0.7528	Intermediate Similarity	NPD7334	Approved
0.7528	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD7521	Approved
0.7528	Intermediate Similarity	NPD6409	Approved
0.7528	Intermediate Similarity	NPD5330	Approved
0.7528	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5693	Phase 1
0.7475	Intermediate Similarity	NPD6008	Approved
0.7391	Intermediate Similarity	NPD5692	Phase 3
0.7342	Intermediate Similarity	NPD4224	Phase 2
0.734	Intermediate Similarity	NPD7900	Approved
0.734	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6050	Approved
0.7312	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD4221	Approved
0.7273	Intermediate Similarity	NPD6052	Approved
0.7234	Intermediate Similarity	NPD6399	Phase 3
0.7222	Intermediate Similarity	NPD1694	Approved
0.7216	Intermediate Similarity	NPD5696	Approved
0.7158	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7128	Intermediate Similarity	NPD5284	Approved
0.7128	Intermediate Similarity	NPD5281	Approved
0.7113	Intermediate Similarity	NPD7902	Approved
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7111	Intermediate Similarity	NPD4197	Approved
0.7108	Intermediate Similarity	NPD5777	Approved
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7079	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5697	Approved
0.7033	Intermediate Similarity	NPD5329	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD6011	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6988	Remote Similarity	NPD4747	Approved
0.6988	Remote Similarity	NPD4691	Approved
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6957	Remote Similarity	NPD4690	Approved
0.6957	Remote Similarity	NPD5205	Approved
0.6957	Remote Similarity	NPD5690	Phase 2
0.6957	Remote Similarity	NPD4693	Phase 3
0.6957	Remote Similarity	NPD4689	Approved
0.6957	Remote Similarity	NPD4138	Approved
0.6957	Remote Similarity	NPD4688	Approved
0.6952	Remote Similarity	NPD6649	Approved
0.6952	Remote Similarity	NPD6650	Approved
0.6951	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5360	Phase 3
0.6947	Remote Similarity	NPD6079	Approved
0.6947	Remote Similarity	NPD7515	Phase 2
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD6373	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6915	Remote Similarity	NPD5328	Approved
0.6907	Remote Similarity	NPD5654	Approved
0.6905	Remote Similarity	NPD6081	Approved
0.6893	Remote Similarity	NPD6614	Approved
0.6893	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD4202	Approved
0.6867	Remote Similarity	NPD4137	Phase 3
0.686	Remote Similarity	NPD3702	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6818	Remote Similarity	NPD3617	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6847	Approved
0.6782	Remote Similarity	NPD6117	Approved
0.6774	Remote Similarity	NPD5280	Approved
0.6774	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD5959	Approved
0.6744	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4058	Approved
0.6742	Remote Similarity	NPD4195	Approved
0.6739	Remote Similarity	NPD3665	Phase 1
0.6739	Remote Similarity	NPD3666	Approved
0.6739	Remote Similarity	NPD3133	Approved
0.6739	Remote Similarity	NPD4786	Approved
0.6737	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD4629	Approved
0.6735	Remote Similarity	NPD5210	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6706	Remote Similarity	NPD4758	Discontinued
0.6705	Remote Similarity	NPD6116	Phase 1
0.6703	Remote Similarity	NPD3667	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6696	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD4696	Approved
0.6634	Remote Similarity	NPD5286	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6634	Remote Similarity	NPD5285	Approved
0.6629	Remote Similarity	NPD6114	Approved
0.6629	Remote Similarity	NPD6115	Approved
0.6629	Remote Similarity	NPD6697	Approved
0.6629	Remote Similarity	NPD6118	Approved
0.66	Remote Similarity	NPD4755	Approved
0.66	Remote Similarity	NPD5173	Approved
0.6596	Remote Similarity	NPD4623	Approved
0.6596	Remote Similarity	NPD4519	Discontinued
0.6593	Remote Similarity	NPD4692	Approved
0.6593	Remote Similarity	NPD4139	Approved
0.6569	Remote Similarity	NPD5223	Approved
0.6562	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3668	Phase 3
0.6552	Remote Similarity	NPD5733	Approved
0.6552	Remote Similarity	NPD4687	Approved
0.6548	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6274	Approved
0.6514	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD5276	Approved
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5224	Approved
0.6505	Remote Similarity	NPD5225	Approved
0.6505	Remote Similarity	NPD5211	Phase 2
0.6505	Remote Similarity	NPD4633	Approved
0.6505	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD7732	Phase 3
0.6486	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5174	Approved
0.6442	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD6314	Approved
0.6429	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD6313	Approved
0.6421	Remote Similarity	NPD5279	Phase 3
0.6396	Remote Similarity	NPD6868	Approved
0.6395	Remote Similarity	NPD4789	Approved
0.6392	Remote Similarity	NPD6051	Approved
0.6386	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5141	Approved
0.6379	Remote Similarity	NPD7492	Approved
0.6373	Remote Similarity	NPD4225	Approved
0.6372	Remote Similarity	NPD7100	Approved
0.6372	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD7736	Approved
0.6346	Remote Similarity	NPD5091	Approved
0.6339	Remote Similarity	NPD6009	Approved
0.6337	Remote Similarity	NPD7614	Phase 1
0.6327	Remote Similarity	NPD4096	Approved
0.6325	Remote Similarity	NPD6616	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6316	Remote Similarity	NPD6319	Approved
0.6304	Remote Similarity	NPD7525	Registered
0.6292	Remote Similarity	NPD3703	Phase 2
0.6286	Remote Similarity	NPD4754	Approved
0.6279	Remote Similarity	NPD3698	Phase 2
0.6271	Remote Similarity	NPD7078	Approved
0.6264	Remote Similarity	NPD5364	Discontinued
0.6262	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5983	Phase 2
0.6261	Remote Similarity	NPD6015	Approved
0.6261	Remote Similarity	NPD6016	Approved
0.6216	Remote Similarity	NPD8133	Approved
0.6207	Remote Similarity	NPD4245	Approved
0.6207	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD4244	Approved
0.6207	Remote Similarity	NPD6370	Approved
0.6204	Remote Similarity	NPD5128	Approved
0.6204	Remote Similarity	NPD4730	Approved
0.6204	Remote Similarity	NPD4729	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