NPASS Compound

Structure

NPC469743 OpenBabel07101718232D 26 31 0 0 1 0 0 0 0 0999 V2000 -2.5921 -0.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5528 0.1973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4003 0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3324 -0.1061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0274 0.5790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7410 0.5296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3771 -1.2669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2570 -0.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0276 -1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0998 -0.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9595 -0.0669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7669 0.3035 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8069 0.2757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0313 -0.6927 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6808 -0.3178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6808 -0.6927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3561 -0.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9480 -0.1156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0313 -0.3178 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1928 -0.0423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4340 0.2365 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6017 -1.0825 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.2625 0.8337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4495 0.7242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6128 -0.8626 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 25 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 13 2 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 22 1 0 0 0 0 10 19 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 1 0 0 0 13 21 1 0 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 22 1 1 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 18 1 6 0 0 0 20 24 1 1 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.16
Volume:	347.11
LogP:	2.058
LogD:	1.818
LogS:	-3.071
# Rotatable Bonds:	2
TPSA:	74.79
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	5.792
Fsp3:	0.55
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:	-5.238
MDCK Permeability:	1.204380805575056e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.849
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.256

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.939
Plasma Protein Binding (PPB):	69.88581848144531%
Volume Distribution (VD):	3.497
Pgp-substrate:	41.804527282714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.131
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.518
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	7.786
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.323
Human Hepatotoxicity (H-HT):	0.708
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.439
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.096
Carcinogencity:	0.87
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC469743

Natural Product ID:	NPC469743
*Common Name:**	Alpneumine F
IUPAC Name:	n.a.
Synonyms:	Alpneumine F
Standard InCHIKey:	ASELQGFIWGKGJJ-KCFDGDNXSA-N
Standard InCHI:	InChI=1S/C20H22N2O4/c1-25-18(23)19-10-26-20(24)12-6-8-22(9-7-14(19)20)16(12)15-11-4-2-3-5-13(11)21-17(15)19/h2-5,12,14,16,21,24H,6-10H2,1H3/t12-,14-,16+,19-,20+/m0/s1
SMILES:	COC(=O)C12COC3(C1CCN4CCC3C4C5=C2NC6=CC=CC=C65)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165402
PubChem CID:	46906305
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO25579	Alstonia pneumatophora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20576577]
NPO25579	Alstonia pneumatophora	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	100000.0	nM	PMID[483600]

☑ 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 NPC469743 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	277
0.1-0.2	1517
0.2-0.3	8175
0.3-0.4	22906
0.4-0.5	5096
0.5-0.6	2825
0.6-0.7	1540
0.7-0.8	339
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC162730
0.8477	Intermediate Similarity	NPC474116
0.8469	Intermediate Similarity	NPC214428
0.8465	Intermediate Similarity	NPC475778
0.8442	Intermediate Similarity	NPC277350
0.8418	Intermediate Similarity	NPC241024
0.8394	Intermediate Similarity	NPC55493
0.8385	Intermediate Similarity	NPC314333
0.8385	Intermediate Similarity	NPC329858
0.8276	Intermediate Similarity	NPC234999
0.8274	Intermediate Similarity	NPC52557
0.8144	Intermediate Similarity	NPC175474
0.8068	Intermediate Similarity	NPC229348
0.803	Intermediate Similarity	NPC475847
0.803	Intermediate Similarity	NPC185742
0.799	Intermediate Similarity	NPC469928
0.7921	Intermediate Similarity	NPC313985
0.7921	Intermediate Similarity	NPC49196
0.7921	Intermediate Similarity	NPC195461
0.7921	Intermediate Similarity	NPC81654
0.7921	Intermediate Similarity	NPC249150
0.7921	Intermediate Similarity	NPC79129
0.7905	Intermediate Similarity	NPC330009
0.7857	Intermediate Similarity	NPC235684
0.7857	Intermediate Similarity	NPC474412
0.785	Intermediate Similarity	NPC474121
0.7843	Intermediate Similarity	NPC137589
0.7822	Intermediate Similarity	NPC50503
0.7755	Intermediate Similarity	NPC472119
0.7711	Intermediate Similarity	NPC81802
0.7711	Intermediate Similarity	NPC247735
0.7711	Intermediate Similarity	NPC472210
0.7711	Intermediate Similarity	NPC269886
0.7711	Intermediate Similarity	NPC472295
0.768	Intermediate Similarity	NPC111275
0.767	Intermediate Similarity	NPC193761
0.7664	Intermediate Similarity	NPC96321
0.7647	Intermediate Similarity	NPC474192
0.7647	Intermediate Similarity	NPC475720
0.7642	Intermediate Similarity	NPC472291
0.7641	Intermediate Similarity	NPC219336
0.7638	Intermediate Similarity	NPC472323
0.7619	Intermediate Similarity	NPC478158
0.7612	Intermediate Similarity	NPC472097
0.7608	Intermediate Similarity	NPC477065
0.7606	Intermediate Similarity	NPC478157
0.7602	Intermediate Similarity	NPC469896
0.76	Intermediate Similarity	NPC196251
0.76	Intermediate Similarity	NPC102338
0.76	Intermediate Similarity	NPC111602
0.76	Intermediate Similarity	NPC63199
0.759	Intermediate Similarity	NPC183662
0.759	Intermediate Similarity	NPC217372
0.759	Intermediate Similarity	NPC15573
0.7588	Intermediate Similarity	NPC315555
0.7585	Intermediate Similarity	NPC476874
0.7585	Intermediate Similarity	NPC476073
0.7581	Intermediate Similarity	NPC473041
0.7577	Intermediate Similarity	NPC329688
0.7577	Intermediate Similarity	NPC189812
0.7574	Intermediate Similarity	NPC472113
0.7574	Intermediate Similarity	NPC472292
0.7563	Intermediate Similarity	NPC71037
0.7562	Intermediate Similarity	NPC472112
0.7559	Intermediate Similarity	NPC54744
0.7549	Intermediate Similarity	NPC472293
0.7546	Intermediate Similarity	NPC52254
0.7538	Intermediate Similarity	NPC267885
0.7534	Intermediate Similarity	NPC70155
0.7534	Intermediate Similarity	NPC473105
0.7524	Intermediate Similarity	NPC293917
0.7524	Intermediate Similarity	NPC472297
0.7524	Intermediate Similarity	NPC472296
0.7522	Intermediate Similarity	NPC475816
0.7513	Intermediate Similarity	NPC91179
0.7512	Intermediate Similarity	NPC321708
0.7511	Intermediate Similarity	NPC311906
0.75	Intermediate Similarity	NPC187255
0.75	Intermediate Similarity	NPC82070
0.7488	Intermediate Similarity	NPC476114
0.7487	Intermediate Similarity	NPC110500
0.7487	Intermediate Similarity	NPC149155
0.7487	Intermediate Similarity	NPC203468
0.7477	Intermediate Similarity	NPC2395
0.7476	Intermediate Similarity	NPC67288
0.7462	Intermediate Similarity	NPC55772
0.7462	Intermediate Similarity	NPC213468
0.7462	Intermediate Similarity	NPC248041
0.7462	Intermediate Similarity	NPC126709
0.7462	Intermediate Similarity	NPC283219
0.7461	Intermediate Similarity	NPC78020
0.7455	Intermediate Similarity	NPC235885
0.7454	Intermediate Similarity	NPC249428
0.7444	Intermediate Similarity	NPC474877
0.7442	Intermediate Similarity	NPC313640
0.7437	Intermediate Similarity	NPC19679
0.7437	Intermediate Similarity	NPC139291
0.7437	Intermediate Similarity	NPC472108
0.7436	Intermediate Similarity	NPC478080
0.7432	Intermediate Similarity	NPC33949
0.7426	Intermediate Similarity	NPC46413
0.7424	Intermediate Similarity	NPC15840
0.7421	Intermediate Similarity	NPC472762
0.7416	Intermediate Similarity	NPC155143
0.7416	Intermediate Similarity	NPC260900
0.7415	Intermediate Similarity	NPC220151
0.7415	Intermediate Similarity	NPC19692
0.7411	Intermediate Similarity	NPC145885
0.7411	Intermediate Similarity	NPC14113
0.7411	Intermediate Similarity	NPC84827
0.7409	Intermediate Similarity	NPC475271
0.7407	Intermediate Similarity	NPC285469
0.7404	Intermediate Similarity	NPC312870
0.7404	Intermediate Similarity	NPC294909
0.7404	Intermediate Similarity	NPC254240
0.7404	Intermediate Similarity	NPC199851
0.7404	Intermediate Similarity	NPC252338
0.7404	Intermediate Similarity	NPC128265
0.7402	Intermediate Similarity	NPC67551
0.7399	Intermediate Similarity	NPC470729
0.7399	Intermediate Similarity	NPC477176
0.7387	Intermediate Similarity	NPC113626
0.7379	Intermediate Similarity	NPC245916
0.7371	Intermediate Similarity	NPC107077
0.7371	Intermediate Similarity	NPC162860
0.7371	Intermediate Similarity	NPC317430
0.7371	Intermediate Similarity	NPC223791
0.7368	Intermediate Similarity	NPC475506
0.7366	Intermediate Similarity	NPC192306
0.7363	Intermediate Similarity	NPC79062
0.7363	Intermediate Similarity	NPC472107
0.7358	Intermediate Similarity	NPC257175
0.7358	Intermediate Similarity	NPC54420
0.735	Intermediate Similarity	NPC469358
0.7349	Intermediate Similarity	NPC75634
0.7349	Intermediate Similarity	NPC151976
0.7349	Intermediate Similarity	NPC87856
0.7346	Intermediate Similarity	NPC473376
0.7343	Intermediate Similarity	NPC227582
0.7339	Intermediate Similarity	NPC174788
0.733	Intermediate Similarity	NPC276517
0.7327	Intermediate Similarity	NPC203614
0.7327	Intermediate Similarity	NPC204491
0.7327	Intermediate Similarity	NPC74969
0.7327	Intermediate Similarity	NPC132211
0.7323	Intermediate Similarity	NPC234987
0.7319	Intermediate Similarity	NPC329982
0.7315	Intermediate Similarity	NPC267965
0.7313	Intermediate Similarity	NPC472294
0.731	Intermediate Similarity	NPC472586
0.7308	Intermediate Similarity	NPC473640
0.7308	Intermediate Similarity	NPC171317
0.7308	Intermediate Similarity	NPC306376
0.7308	Intermediate Similarity	NPC131887
0.7304	Intermediate Similarity	NPC469470
0.7304	Intermediate Similarity	NPC469501
0.7302	Intermediate Similarity	NPC82370
0.7299	Intermediate Similarity	NPC476115
0.7295	Intermediate Similarity	NPC11445
0.7294	Intermediate Similarity	NPC472285
0.729	Intermediate Similarity	NPC271862
0.7286	Intermediate Similarity	NPC472443
0.7282	Intermediate Similarity	NPC267343
0.7277	Intermediate Similarity	NPC474905
0.7273	Intermediate Similarity	NPC74413
0.7264	Intermediate Similarity	NPC472444
0.726	Intermediate Similarity	NPC281049
0.7259	Intermediate Similarity	NPC472123
0.7256	Intermediate Similarity	NPC471304
0.7255	Intermediate Similarity	NPC213629
0.7254	Intermediate Similarity	NPC16667
0.7252	Intermediate Similarity	NPC64216
0.7252	Intermediate Similarity	NPC266192
0.7248	Intermediate Similarity	NPC85702
0.7248	Intermediate Similarity	NPC148183
0.7248	Intermediate Similarity	NPC152768
0.7248	Intermediate Similarity	NPC36405
0.7246	Intermediate Similarity	NPC181502
0.7246	Intermediate Similarity	NPC85066
0.7246	Intermediate Similarity	NPC157828
0.7246	Intermediate Similarity	NPC57994
0.7246	Intermediate Similarity	NPC195239
0.7246	Intermediate Similarity	NPC289299
0.7243	Intermediate Similarity	NPC127677
0.7243	Intermediate Similarity	NPC258062
0.7241	Intermediate Similarity	NPC81939
0.7241	Intermediate Similarity	NPC62749
0.7234	Intermediate Similarity	NPC14812
0.7231	Intermediate Similarity	NPC326479
0.723	Intermediate Similarity	NPC18661
0.7229	Intermediate Similarity	NPC473540
0.7225	Intermediate Similarity	NPC102008
0.7225	Intermediate Similarity	NPC195457
0.722	Intermediate Similarity	NPC154339
0.7217	Intermediate Similarity	NPC476098
0.7217	Intermediate Similarity	NPC98715
0.7215	Intermediate Similarity	NPC312645
0.7212	Intermediate Similarity	NPC14288
0.7212	Intermediate Similarity	NPC475969
0.7212	Intermediate Similarity	NPC475859

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 NPC469743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	486
0.2-0.3	822
0.3-0.4	1939
0.4-0.5	3175
0.5-0.6	2067
0.6-0.7	431
0.7-0.8	62
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
0.8385	Intermediate Similarity	NPD4499	Approved
0.7921	Intermediate Similarity	NPD4600	Approved
0.7921	Intermediate Similarity	NPD4601	Approved
0.7767	Intermediate Similarity	NPD8098	Approved
0.7737	Intermediate Similarity	NPD2844	Phase 3
0.7685	Intermediate Similarity	NPD5003	Discontinued
0.7614	Intermediate Similarity	NPD2095	Phase 2
0.7614	Intermediate Similarity	NPD2092	Phase 2
0.7614	Intermediate Similarity	NPD2094	Phase 2
0.7596	Intermediate Similarity	NPD8282	Approved
0.7596	Intermediate Similarity	NPD56	Approved
0.7596	Intermediate Similarity	NPD8283	Approved
0.7576	Intermediate Similarity	NPD2096	Phase 2
0.7576	Intermediate Similarity	NPD2091	Phase 2
0.7547	Intermediate Similarity	NPD7470	Discontinued
0.7524	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD8096	Phase 3
0.7512	Intermediate Similarity	NPD8097	Phase 3
0.7512	Intermediate Similarity	NPD5426	Phase 3
0.7488	Intermediate Similarity	NPD8423	Phase 2
0.7488	Intermediate Similarity	NPD8399	Phase 1
0.7487	Intermediate Similarity	NPD482	Approved
0.7475	Intermediate Similarity	NPD2565	Phase 2
0.7475	Intermediate Similarity	NPD2564	Approved
0.7465	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD8072	Approved
0.7464	Intermediate Similarity	NPD6176	Phase 1
0.7453	Intermediate Similarity	NPD7941	Phase 3
0.7449	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD2510	Approved
0.7406	Intermediate Similarity	NPD2509	Approved
0.7404	Intermediate Similarity	NPD4500	Approved
0.7404	Intermediate Similarity	NPD4501	Approved
0.7391	Intermediate Similarity	NPD7946	Pre-registration
0.735	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD750	Phase 2
0.7333	Intermediate Similarity	NPD8073	Approved
0.7327	Intermediate Similarity	NPD8160	Phase 2
0.7323	Intermediate Similarity	NPD7865	Approved
0.7311	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7957	Phase 1
0.7281	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4602	Approved
0.723	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7001	Phase 3
0.723	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD53	Approved
0.7225	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7777	Approved
0.7225	Intermediate Similarity	NPD7778	Approved
0.7206	Intermediate Similarity	NPD8466	Approved
0.7206	Intermediate Similarity	NPD8429	Approved
0.7206	Intermediate Similarity	NPD8428	Approved
0.7206	Intermediate Similarity	NPD8467	Approved
0.7206	Intermediate Similarity	NPD8427	Approved
0.7206	Intermediate Similarity	NPD4948	Discontinued
0.7206	Intermediate Similarity	NPD8465	Approved
0.719	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5901	Discontinued
0.7179	Intermediate Similarity	NPD8358	Approved
0.7171	Intermediate Similarity	NPD1534	Approved
0.7157	Intermediate Similarity	NPD1573	Approved
0.7157	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1575	Approved
0.7136	Intermediate Similarity	NPD2920	Discontinued
0.7129	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7878	Phase 2
0.7102	Intermediate Similarity	NPD8364	Approved
0.7102	Intermediate Similarity	NPD8363	Approved
0.7093	Intermediate Similarity	NPD7824	Approved
0.7092	Intermediate Similarity	NPD8459	Approved
0.7092	Intermediate Similarity	NPD8460	Approved
0.7092	Intermediate Similarity	NPD8425	Approved
0.7092	Intermediate Similarity	NPD8426	Approved
0.7087	Intermediate Similarity	NPD4334	Discontinued
0.7083	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4427	Phase 2
0.7079	Intermediate Similarity	NPD5897	Approved
0.7079	Intermediate Similarity	NPD5899	Approved
0.7079	Intermediate Similarity	NPD5898	Approved
0.7075	Intermediate Similarity	NPD484	Approved
0.7065	Intermediate Similarity	NPD2144	Approved
0.7062	Intermediate Similarity	NPD4397	Phase 1
0.7056	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4506	Discontinued
0.7045	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD7970	Approved
0.7045	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3038	Discontinued
0.7035	Intermediate Similarity	NPD7711	Discontinued
0.7032	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6999	Discontinued
0.7028	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5471	Phase 3
0.7014	Intermediate Similarity	NPD3389	Approved
0.7014	Intermediate Similarity	NPD3393	Approved
0.7014	Intermediate Similarity	NPD3394	Approved
0.701	Intermediate Similarity	NPD5596	Phase 2
0.7009	Intermediate Similarity	NPD7770	Phase 3
0.7004	Intermediate Similarity	NPD7730	Approved
0.7004	Intermediate Similarity	NPD7731	Approved
0.7004	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7950	Approved
0.7	Intermediate Similarity	NPD7951	Approved
0.7	Intermediate Similarity	NPD7789	Approved
0.7	Intermediate Similarity	NPD7952	Approved
0.7	Intermediate Similarity	NPD7791	Approved
0.7	Intermediate Similarity	NPD7953	Approved
0.7	Intermediate Similarity	NPD7790	Approved
0.6996	Remote Similarity	NPD6770	Approved
0.6995	Remote Similarity	NPD6595	Phase 3
0.6991	Remote Similarity	NPD7271	Approved
0.6985	Remote Similarity	NPD1325	Approved
0.6985	Remote Similarity	NPD1326	Approved
0.6982	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6995	Phase 1
0.6965	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8322	Phase 2
0.6948	Remote Similarity	NPD6249	Phase 2
0.6948	Remote Similarity	NPD6248	Phase 2
0.6944	Remote Similarity	NPD6987	Phase 1
0.6944	Remote Similarity	NPD3947	Discontinued
0.6941	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7866	Approved
0.6927	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4315	Phase 2
0.69	Remote Similarity	NPD7781	Approved
0.69	Remote Similarity	NPD7780	Approved
0.6881	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7717	Approved
0.6872	Remote Similarity	NPD7716	Approved
0.6869	Remote Similarity	NPD1631	Approved
0.6869	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5140	Approved
0.6869	Remote Similarity	NPD5138	Approved
0.6866	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8272	Phase 2
0.686	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7665	Phase 2
0.6849	Remote Similarity	NPD7666	Phase 3
0.6842	Remote Similarity	NPD7234	Approved
0.6842	Remote Similarity	NPD7233	Approved
0.684	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7688	Phase 1
0.6818	Remote Similarity	NPD4520	Approved
0.681	Remote Similarity	NPD4885	Approved
0.6806	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7864	Approved
0.6794	Remote Similarity	NPD8489	Phase 1
0.6786	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6978	Phase 2
0.6783	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8386	Phase 2
0.6773	Remote Similarity	NPD2916	Discontinued
0.6769	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7769	Phase 3
0.6762	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7619	Phase 3
0.6761	Remote Similarity	NPD7618	Phase 3
0.6761	Remote Similarity	NPD7944	Discontinued
0.6756	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD8325	Phase 3
0.6756	Remote Similarity	NPD8326	Phase 3
0.6754	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD1592	Phase 3
0.6732	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7727	Phase 2
0.6727	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5632	Approved
0.6726	Remote Similarity	NPD4852	Phase 2
0.6717	Remote Similarity	NPD1630	Approved
0.6716	Remote Similarity	NPD5065	Approved
0.6716	Remote Similarity	NPD7863	Approved
0.6714	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4373	Phase 2
0.6707	Remote Similarity	NPD7956	Approved
0.6707	Remote Similarity	NPD7955	Approved
0.6699	Remote Similarity	NPD4079	Approved
0.6699	Remote Similarity	NPD4076	Approved
0.6698	Remote Similarity	NPD5913	Phase 3
0.6698	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6455	Phase 3
0.6683	Remote Similarity	NPD3319	Phase 1
0.6683	Remote Similarity	NPD3320	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