NPASS Compound

Structure

CID321211 OpenBabel06191716152D 27 32 0 0 1 0 0 0 0 0999 V2000 -2.1598 3.5109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6711 -2.0145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2411 -1.2299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4441 -0.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7065 -1.9132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8467 -0.3439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8741 0.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2659 0.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2961 0.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2961 -1.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8741 -1.0272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2659 -1.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3020 1.0571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3121 -1.0272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2600 1.0571 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8821 -0.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3248 0.8923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9115 2.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9517 0.2424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6103 0.2424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6103 -0.7275 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9517 -0.7275 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.3121 0.5421 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2985 1.6353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2625 3.1076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8601 2.5885 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 26 1 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 14 2 0 0 0 0 6 16 2 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 1 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 19 22 1 6 0 0 0 20 21 1 6 0 0 0 20 23 1 0 0 0 0 21 10 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.16
Volume:	361.769
LogP:	2.492
LogD:	1.913
LogS:	-5.161
# Rotatable Bonds:	2
TPSA:	59.08
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	6.61
Fsp3:	0.524
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:	-4.836
MDCK Permeability:	2.3640815925318748e-05
Pgp-inhibitor:	0.7
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.659
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.975
Plasma Protein Binding (PPB):	31.84156036376953%
Volume Distribution (VD):	1.336
Pgp-substrate:	66.61137390136719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.612
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.613
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.419
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	5.404
Half-life (T1/2):	0.474

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.831
Drug-inuced Liver Injury (DILI):	0.746
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.133
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC321211

Natural Product ID:	NPC321211
*Common Name:**	Lapidilectine B
IUPAC Name:	n.a.
Synonyms:	Lapidilectine B
Standard InCHIKey:	GLOIILVAVSJIEX-LWILDLIXSA-N
Standard InCHI:	InChI=1S/C21H22N2O4/c1-26-18(25)23-16-6-3-2-5-14(16)21-10-12-22-11-4-7-19(22)8-9-20(21,23)15(13-19)17(24)27-21/h2-7,15H,8-13H2,1H3/t15-,19+,20+,21+/m0/s1
SMILES:	COC(=O)N1c2ccccc2[C@@]23[C@@]41CC[C@@]1(C[C@H]4C(=O)O3)C=CCN1CC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801887
PubChem CID:	12138542
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives [CHEMONTID:0002406] Indolecarboxylic acids

*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
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	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	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT22764	CELL-LINE	KB/VJ300	Homo sapiens	IC50	=	0.39	ug.mL-1	PMID[459624]

☑ 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 NPC321211 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	312
0.1-0.2	1424
0.2-0.3	5461
0.3-0.4	17548
0.4-0.5	13196
0.5-0.6	4249
0.6-0.7	480
0.7-0.8	24
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9695	High Similarity	NPC322621
0.8323	Intermediate Similarity	NPC201424
0.7791	Intermediate Similarity	NPC225319
0.7487	Intermediate Similarity	NPC473298
0.7443	Intermediate Similarity	NPC99632
0.7443	Intermediate Similarity	NPC282339
0.7416	Intermediate Similarity	NPC472115
0.7416	Intermediate Similarity	NPC472114
0.7401	Intermediate Similarity	NPC313757
0.738	Intermediate Similarity	NPC181928
0.7354	Intermediate Similarity	NPC25401
0.7348	Intermediate Similarity	NPC251212
0.7348	Intermediate Similarity	NPC214626
0.7348	Intermediate Similarity	NPC139085
0.7287	Intermediate Similarity	NPC21425
0.7287	Intermediate Similarity	NPC14994
0.7268	Intermediate Similarity	NPC129624
0.7267	Intermediate Similarity	NPC242000
0.7257	Intermediate Similarity	NPC161827
0.7253	Intermediate Similarity	NPC96901
0.724	Intermediate Similarity	NPC34717
0.7222	Intermediate Similarity	NPC278887
0.7213	Intermediate Similarity	NPC13367
0.7202	Intermediate Similarity	NPC473375
0.7202	Intermediate Similarity	NPC97100
0.7191	Intermediate Similarity	NPC248117
0.7167	Intermediate Similarity	NPC52059
0.7167	Intermediate Similarity	NPC470069
0.7166	Intermediate Similarity	NPC159963
0.7165	Intermediate Similarity	NPC90967
0.7158	Intermediate Similarity	NPC307640
0.7157	Intermediate Similarity	NPC234772
0.7151	Intermediate Similarity	NPC293458
0.7151	Intermediate Similarity	NPC11149
0.715	Intermediate Similarity	NPC221687
0.7143	Intermediate Similarity	NPC138830
0.7136	Intermediate Similarity	NPC288110
0.7135	Intermediate Similarity	NPC263709
0.7135	Intermediate Similarity	NPC310403
0.7135	Intermediate Similarity	NPC97380
0.7135	Intermediate Similarity	NPC148468
0.7135	Intermediate Similarity	NPC193410
0.7135	Intermediate Similarity	NPC63210
0.7135	Intermediate Similarity	NPC186669
0.7135	Intermediate Similarity	NPC243673
0.712	Intermediate Similarity	NPC105055
0.712	Intermediate Similarity	NPC474059
0.712	Intermediate Similarity	NPC22689
0.7119	Intermediate Similarity	NPC29285
0.709	Intermediate Similarity	NPC52262
0.7088	Intermediate Similarity	NPC224970
0.7088	Intermediate Similarity	NPC167724
0.7088	Intermediate Similarity	NPC223595
0.7081	Intermediate Similarity	NPC264482
0.7081	Intermediate Similarity	NPC203202
0.7079	Intermediate Similarity	NPC123241
0.7079	Intermediate Similarity	NPC113946
0.7079	Intermediate Similarity	NPC61013
0.7076	Intermediate Similarity	NPC308197
0.7065	Intermediate Similarity	NPC285192
0.7065	Intermediate Similarity	NPC177261
0.7056	Intermediate Similarity	NPC475489
0.7056	Intermediate Similarity	NPC67904
0.7056	Intermediate Similarity	NPC286871
0.7053	Intermediate Similarity	NPC222046
0.7043	Intermediate Similarity	NPC260075
0.7039	Intermediate Similarity	NPC244425
0.7039	Intermediate Similarity	NPC15384
0.7005	Intermediate Similarity	NPC471198
0.7	Intermediate Similarity	NPC143457
0.7	Intermediate Similarity	NPC474058
0.6983	Remote Similarity	NPC153694
0.6983	Remote Similarity	NPC211525
0.6973	Remote Similarity	NPC476425
0.6963	Remote Similarity	NPC35390
0.6963	Remote Similarity	NPC470631
0.6963	Remote Similarity	NPC473781
0.6963	Remote Similarity	NPC282092
0.6961	Remote Similarity	NPC476231
0.6957	Remote Similarity	NPC469915
0.6957	Remote Similarity	NPC471197
0.6947	Remote Similarity	NPC97584
0.6944	Remote Similarity	NPC471122
0.6935	Remote Similarity	NPC471512
0.693	Remote Similarity	NPC473486
0.693	Remote Similarity	NPC475316
0.6927	Remote Similarity	NPC127996
0.6923	Remote Similarity	NPC470485
0.6915	Remote Similarity	NPC6974
0.691	Remote Similarity	NPC478076
0.6907	Remote Similarity	NPC22476
0.6904	Remote Similarity	NPC162440
0.6901	Remote Similarity	NPC473458
0.6888	Remote Similarity	NPC243626
0.6887	Remote Similarity	NPC231924
0.6885	Remote Similarity	NPC471124
0.6885	Remote Similarity	NPC472106
0.6882	Remote Similarity	NPC21752
0.6882	Remote Similarity	NPC276993
0.6882	Remote Similarity	NPC293255
0.6882	Remote Similarity	NPC298851
0.6882	Remote Similarity	NPC181138
0.6882	Remote Similarity	NPC285622
0.6882	Remote Similarity	NPC210415
0.6881	Remote Similarity	NPC277350
0.6872	Remote Similarity	NPC473004
0.6868	Remote Similarity	NPC85651
0.6868	Remote Similarity	NPC176983
0.6868	Remote Similarity	NPC472120
0.6868	Remote Similarity	NPC472101
0.6868	Remote Similarity	NPC472117
0.6856	Remote Similarity	NPC5630
0.6845	Remote Similarity	NPC329338
0.6845	Remote Similarity	NPC469726
0.6842	Remote Similarity	NPC475962
0.6839	Remote Similarity	NPC473815
0.6837	Remote Similarity	NPC477397
0.6825	Remote Similarity	NPC218594
0.6825	Remote Similarity	NPC99043
0.6822	Remote Similarity	NPC471513
0.6821	Remote Similarity	NPC203628
0.6821	Remote Similarity	NPC470483
0.6813	Remote Similarity	NPC309531
0.6813	Remote Similarity	NPC315368
0.6813	Remote Similarity	NPC472102
0.6806	Remote Similarity	NPC477159
0.6784	Remote Similarity	NPC100863
0.6784	Remote Similarity	NPC132874
0.6784	Remote Similarity	NPC218733
0.6784	Remote Similarity	NPC138615
0.6784	Remote Similarity	NPC265642
0.6778	Remote Similarity	NPC473297
0.6771	Remote Similarity	NPC245741
0.6769	Remote Similarity	NPC473569
0.6763	Remote Similarity	NPC159815
0.6762	Remote Similarity	NPC77777
0.6758	Remote Similarity	NPC36495
0.6757	Remote Similarity	NPC214960
0.6757	Remote Similarity	NPC279527
0.6751	Remote Similarity	NPC203972
0.6749	Remote Similarity	NPC268077
0.6744	Remote Similarity	NPC319645
0.6736	Remote Similarity	NPC49184
0.6734	Remote Similarity	NPC302548
0.6729	Remote Similarity	NPC477394
0.672	Remote Similarity	NPC320147
0.672	Remote Similarity	NPC476441
0.6717	Remote Similarity	NPC230313
0.6716	Remote Similarity	NPC195787
0.6716	Remote Similarity	NPC246140
0.6716	Remote Similarity	NPC214428
0.6704	Remote Similarity	NPC243756
0.6701	Remote Similarity	NPC204970
0.67	Remote Similarity	NPC207971
0.6684	Remote Similarity	NPC476326
0.6683	Remote Similarity	NPC232600
0.6683	Remote Similarity	NPC10732
0.6683	Remote Similarity	NPC478075
0.6683	Remote Similarity	NPC303214
0.6667	Remote Similarity	NPC14339
0.6667	Remote Similarity	NPC475147
0.6667	Remote Similarity	NPC122106
0.6667	Remote Similarity	NPC329833
0.6667	Remote Similarity	NPC192306
0.6667	Remote Similarity	NPC470548
0.665	Remote Similarity	NPC475559
0.665	Remote Similarity	NPC471436
0.665	Remote Similarity	NPC1464
0.6649	Remote Similarity	NPC473007
0.6649	Remote Similarity	NPC259626
0.6636	Remote Similarity	NPC160113
0.6636	Remote Similarity	NPC476220
0.6635	Remote Similarity	NPC473837
0.6633	Remote Similarity	NPC284706
0.6627	Remote Similarity	NPC231382
0.6621	Remote Similarity	NPC139373
0.6618	Remote Similarity	NPC475133
0.6615	Remote Similarity	NPC39822
0.6606	Remote Similarity	NPC154922
0.6601	Remote Similarity	NPC469732
0.6599	Remote Similarity	NPC473008
0.6598	Remote Similarity	NPC2933
0.6587	Remote Similarity	NPC250476
0.6585	Remote Similarity	NPC87714
0.6576	Remote Similarity	NPC301163
0.6573	Remote Similarity	NPC264589
0.657	Remote Similarity	NPC173295
0.6564	Remote Similarity	NPC476095
0.655	Remote Similarity	NPC21483
0.655	Remote Similarity	NPC198205
0.6546	Remote Similarity	NPC256288
0.6545	Remote Similarity	NPC84347
0.6543	Remote Similarity	NPC33507
0.6542	Remote Similarity	NPC318525
0.6542	Remote Similarity	NPC140311
0.6542	Remote Similarity	NPC10653
0.6538	Remote Similarity	NPC477160
0.6537	Remote Similarity	NPC295548
0.6535	Remote Similarity	NPC23080
0.6535	Remote Similarity	NPC71124

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 NPC321211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	570
0.2-0.3	787
0.3-0.4	1587
0.4-0.5	3651
0.5-0.6	2213
0.6-0.7	157
0.7-0.8	0
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
0.7196	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6238	Discontinued
0.7011	Intermediate Similarity	NPD1802	Approved
0.7011	Intermediate Similarity	NPD1801	Approved
0.6982	Remote Similarity	NPD2670	Approved
0.6902	Remote Similarity	NPD6457	Approved
0.6879	Remote Similarity	NPD2820	Phase 3
0.6836	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2365	Approved
0.6821	Remote Similarity	NPD6659	Phase 2
0.6806	Remote Similarity	NPD7688	Phase 1
0.6798	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7570	Approved
0.6786	Remote Similarity	NPD7569	Approved
0.6755	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6891	Phase 2
0.6744	Remote Similarity	NPD1109	Approved
0.6744	Remote Similarity	NPD1110	Approved
0.6744	Remote Similarity	NPD3170	Approved
0.6739	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5997	Discontinued
0.6685	Remote Similarity	NPD5942	Approved
0.6685	Remote Similarity	NPD7528	Approved
0.6685	Remote Similarity	NPD5941	Approved
0.6684	Remote Similarity	NPD5600	Discontinued
0.6667	Remote Similarity	NPD7599	Phase 2
0.665	Remote Similarity	NPD5003	Discontinued
0.6648	Remote Similarity	NPD2387	Approved
0.6648	Remote Similarity	NPD7487	Discontinued
0.6647	Remote Similarity	NPD5993	Phase 1
0.6632	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7478	Approved
0.6612	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7606	Phase 3
0.6608	Remote Similarity	NPD5184	Approved
0.6608	Remote Similarity	NPD5182	Approved
0.6608	Remote Similarity	NPD5185	Approved
0.6599	Remote Similarity	NPD2565	Phase 2
0.6599	Remote Similarity	NPD2564	Approved
0.6591	Remote Similarity	NPD4430	Phase 2
0.6561	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4176	Approved
0.6545	Remote Similarity	NPD4178	Approved
0.6541	Remote Similarity	NPD7600	Phase 2
0.6537	Remote Similarity	NPD2920	Discontinued
0.6528	Remote Similarity	NPD6878	Phase 2
0.6528	Remote Similarity	NPD6879	Phase 2
0.651	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6037	Discontinued
0.6485	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6995	Phase 1
0.6477	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7470	Discontinued
0.6476	Remote Similarity	NPD4493	Discontinued
0.6473	Remote Similarity	NPD7001	Phase 3
0.6467	Remote Similarity	NPD1663	Discontinued
0.6467	Remote Similarity	NPD6571	Approved
0.6467	Remote Similarity	NPD6570	Approved
0.6467	Remote Similarity	NPD7105	Phase 1
0.6465	Remote Similarity	NPD3437	Discontinued
0.6458	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1626	Approved
0.6455	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD3983	Phase 3
0.6453	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD5086	Approved
0.6443	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD2484	Approved
0.6442	Remote Similarity	NPD2485	Approved
0.6439	Remote Similarity	NPD6321	Discontinued
0.6436	Remote Similarity	NPD5430	Discontinued
0.6436	Remote Similarity	NPD7035	Approved
0.6436	Remote Similarity	NPD7036	Phase 3
0.6432	Remote Similarity	NPD5928	Phase 1
0.6429	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7280	Phase 3
0.6429	Remote Similarity	NPD6320	Approved
0.6429	Remote Similarity	NPD7281	Phase 3
0.6425	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3947	Discontinued
0.6421	Remote Similarity	NPD5183	Approved
0.6421	Remote Similarity	NPD5186	Approved
0.6406	Remote Similarity	NPD5466	Approved
0.6406	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5024	Approved
0.64	Remote Similarity	NPD2569	Approved
0.64	Remote Similarity	NPD2567	Approved
0.6396	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4621	Approved
0.6395	Remote Similarity	NPD4619	Approved
0.6389	Remote Similarity	NPD3141	Discontinued
0.6389	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD2093	Discontinued
0.6383	Remote Similarity	NPD8007	Approved
0.6383	Remote Similarity	NPD8008	Approved
0.6379	Remote Similarity	NPD2791	Discontinued
0.6378	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD2836	Approved
0.6376	Remote Similarity	NPD3912	Discontinued
0.6368	Remote Similarity	NPD6723	Discontinued
0.6364	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2790	Discontinued
0.6359	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5582	Discontinued
0.6354	Remote Similarity	NPD7854	Phase 2
0.6354	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD4796	Discontinued
0.6348	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5610	Approved
0.6333	Remote Similarity	NPD4859	Phase 1
0.6333	Remote Similarity	NPD6622	Phase 1
0.633	Remote Similarity	NPD1743	Approved
0.633	Remote Similarity	NPD1742	Approved
0.633	Remote Similarity	NPD19	Approved
0.6324	Remote Similarity	NPD5515	Phase 2
0.6319	Remote Similarity	NPD4888	Discontinued
0.6318	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5913	Phase 3
0.6316	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7179	Phase 2
0.6313	Remote Similarity	NPD1625	Approved
0.6311	Remote Similarity	NPD6805	Discontinued
0.6311	Remote Similarity	NPD5891	Approved
0.6302	Remote Similarity	NPD5633	Discontinued
0.6301	Remote Similarity	NPD7820	Phase 3
0.6298	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD6416	Phase 2
0.6298	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD3625	Discontinued
0.6283	Remote Similarity	NPD2680	Approved
0.6283	Remote Similarity	NPD2681	Approved
0.6278	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6357	Discontinued
0.6269	Remote Similarity	NPD5112	Approved
0.6269	Remote Similarity	NPD5114	Approved
0.6269	Remote Similarity	NPD5113	Approved
0.6267	Remote Similarity	NPD6770	Approved
0.6264	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7248	Discontinued
0.6256	Remote Similarity	NPD2509	Approved
0.6256	Remote Similarity	NPD2510	Approved
0.6256	Remote Similarity	NPD3449	Discontinued
0.625	Remote Similarity	NPD5239	Approved
0.625	Remote Similarity	NPD5240	Approved
0.625	Remote Similarity	NPD5235	Approved
0.625	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5237	Approved
0.625	Remote Similarity	NPD5236	Approved
0.6244	Remote Similarity	NPD7186	Phase 3
0.6243	Remote Similarity	NPD7295	Approved
0.6238	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5994	Discontinued
0.6238	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5076	Approved
0.6238	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5077	Approved
0.6237	Remote Similarity	NPD1093	Approved
0.6237	Remote Similarity	NPD1092	Approved
0.6236	Remote Similarity	NPD989	Approved
0.6224	Remote Similarity	NPD7881	Approved
0.6224	Remote Similarity	NPD7479	Phase 2
0.6223	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7082	Approved
0.6221	Remote Similarity	NPD5204	Approved
0.6221	Remote Similarity	NPD3663	Approved
0.6221	Remote Similarity	NPD3662	Phase 3
0.6221	Remote Similarity	NPD3661	Approved
0.6221	Remote Similarity	NPD3664	Approved
0.622	Remote Similarity	NPD6445	Discontinued
0.622	Remote Similarity	NPD7205	Discontinued
0.6216	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5196	Approved
0.6214	Remote Similarity	NPD5194	Approved
0.6214	Remote Similarity	NPD5197	Approved
0.6211	Remote Similarity	NPD2201	Approved
0.6198	Remote Similarity	NPD2844	Phase 3
0.6197	Remote Similarity	NPD3893	Discontinued
0.6197	Remote Similarity	NPD5860	Discontinued
0.6196	Remote Similarity	NPD7613	Discontinued
0.6195	Remote Similarity	NPD3964	Approved
0.6193	Remote Similarity	NPD3227	Phase 2
0.6193	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7921	Approved
0.619	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7244	Discontinued
0.619	Remote Similarity	NPD6644	Discontinued
0.6188	Remote Similarity	NPD7259	Approved
0.6188	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD4121	Phase 3
0.6183	Remote Similarity	NPD4120	Approved
0.6182	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6070	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